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N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
Cas No: 152460-10-1
No Data 10 Gram 20 Metric Ton/Month Changzhou Sunsanta Chemical Co.,Ltd Contact Supplier
N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
Cas No: 152460-10-1
No Data 1 Kilogram 1000 Kilogram/Month Hangzhou Fortune Biopharm Co.,LTD. Contact Supplier
N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine,High Purity
Cas No: 152460-10-1
No Data 1 Gram 1 Metric Ton/Month Jinan Kangcheng Pharmaceutical Technology Co., Ltd. Contact Supplier
N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine Manufacturer/High quality/Best price/In stock
Cas No: 152460-10-1
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality N-(5-Amino-2-Methylphenyl)-4-(3-Pyridyl)-2-Pyrimidineamine supplier in China
Cas No: 152460-10-1
No Data No Data Metric Ton/Day Simagchem Corporation Contact Supplier
Imatinib intermediates-- N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
Cas No: 152460-10-1
USD $ 2.0-3.0 / Kilogram 1 Kilogram 10 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
152460-10-1 N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
Cas No: 152460-10-1
USD $ 40.0-50.0 / Gram 1 Gram 1000 Metric Ton/Day WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
152460-10-1
Cas No: 152460-10-1
No Data 1 Kilogram 20 Metric Ton/Month Henan Allgreen Chemical Co.,Ltd Contact Supplier
N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
Cas No: 152460-10-1
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
4-Methyl-N3-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine
Cas No: 152460-10-1
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier

152460-10-1 Usage

Uses

Abacavir intermediate

Chemical Properties

Yellow Solid

Uses

A selective inhibitor of protein kinase C (PKC).
InChI:InChI=1/C16H15N5/c1-11-4-5-13(17)9-15(11)21-16-19-8-6-14(20-16)12-3-2-7-18-10-12/h2-10H,17H2,1H3,(H,19,20,21)

152460-10-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (Y0001693)  Imatinib impurity F  EuropePharmacopoeia (EP) Reference Standard 152460-10-1 Y0001693 1,880.19CNY Detail

152460-10-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Methyl-N3-[4-(3-Pyridinyl)-2-Pyrimidinyl]-1,3-Benzenediamine

1.2 Other means of identification

Product number -
Other names 6-Methyl-N1-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:152460-10-1 SDS

152460-10-1Synthetic route

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
152460-09-8

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate for 3h;100%
With palladium on activated charcoal; hydrogen In ethyl acetate at 20℃; for 3h; Inert atmosphere;100%
With hydrazine hydrate In N,N-dimethyl-formamide at 100℃; for 3h; Green chemistry;100%
imatinib
152459-95-5

imatinib

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With hydrogenchloride; acetic acid at 20℃; Reflux;97%
tert-butyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

tert-butyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 8h;95%
(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

(2-methyl-5-aminophenyl)guanidine
581076-64-4

(2-methyl-5-aminophenyl)guanidine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
In butan-1-ol at 70℃;92%
2-bromo-4-nitrotoluene
7745-93-9

2-bromo-4-nitrotoluene

4-pyridin-3-ylpyrimidin-2-ylamine
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Stage #1: 2-bromo-4-nitrotoluene; 4-pyridin-3-ylpyrimidin-2-ylamine With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;
Stage #2: With potassium tert-butylate; bis(pinacol)diborane In 1,4-dioxane; isopropyl alcohol at 110℃; for 4h; Inert atmosphere; chemoselective reaction;
83%
hydrazine hydrate
7803-57-8

hydrazine hydrate

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
152460-09-8

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With iron(III) chloride; pyrographite In water at 80℃; for 6 - 8h;80%
(S)-3-allyl-1-benzoyl-4-(4-methoxybenzyl)-3-methylpiperazin-2-one

(S)-3-allyl-1-benzoyl-4-(4-methoxybenzyl)-3-methylpiperazin-2-one

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 1.5h;75%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 12h; Curtius Rearrangement;
Stage #2: With hydrogenchloride In water; toluene at 100℃;
60%
Multi-step reaction with 2 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C
2: trifluoroacetic acid / dichloromethane / 8 h
View Scheme
SnCl2.2H2O

SnCl2.2H2O

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
152460-09-8

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
In hydrogenchloride46%
methyl-3-pyridylketone
350-03-8

methyl-3-pyridylketone

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / Heating
2: NaOH / propan-2-ol / 24 h / Heating
3: 8.9 g / SnCl2; aq. HCl / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: 92 percent / xylene / 140 °C
2: 92 percent / butan-1-ol / 70 °C
View Scheme
Multi-step reaction with 3 steps
2: 41.3 percent / sodium hydroxide / propan-2-ol / 8 h / Heating
3: 60.9 percent / H2 / palladium on charcoal / tetrahydrofuran / 21 h / 750.06 Torr / Ambient temperature
View Scheme
3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / propan-2-ol / 24 h / Heating
2: 8.9 g / SnCl2; aq. HCl / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-2-pentanone / 12 h / Reflux
2: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: sodium ethanolate / ethanol / 6 h / 78 °C
1.2: 0.17 h / 78 °C
2.1: sodium hydroxide / water
2.2: 20 °C
3.1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C
4.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C
5.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
1-(2-methyl-5-nitrophenyl)guanidine nitrate

1-(2-methyl-5-nitrophenyl)guanidine nitrate

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOH / propan-2-ol / 24 h / Heating
2: 8.9 g / SnCl2; aq. HCl / 0.5 h
View Scheme
Multi-step reaction with 2 steps
1: 41.3 percent / sodium hydroxide / propan-2-ol / 8 h / Heating
2: 60.9 percent / H2 / palladium on charcoal / tetrahydrofuran / 21 h / 750.06 Torr / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: NaOH / propan-2-ol / Heating
2: H2 / 5percent Pd-C / tetrahydrofuran / 750.06 Torr / Ambient temperature
View Scheme
2-methyl-5-nitroaniline
99-55-8

2-methyl-5-nitroaniline

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: HNO3 / ethanol / Heating
2: NaOH / propan-2-ol / 24 h / Heating
3: 8.9 g / SnCl2; aq. HCl / 0.5 h
View Scheme
Multi-step reaction with 3 steps
1: aq. HCl / butan-1-ol / 150 °C
2: H2 / Pd/C / butan-1-ol
3: 92 percent / butan-1-ol / 70 °C
View Scheme
Multi-step reaction with 4 steps
1.1: nitric acid / ethanol / 25 - 50 °C
1.2: 3 h / Reflux
2.1: sodium hydroxide / water
3.1: 4-methyl-2-pentanone / 12 h / Reflux
4.1: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere
View Scheme
1-(2-methyl-5-nitrophenyl)guanidine
152460-07-6

1-(2-methyl-5-nitrophenyl)guanidine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd/C / butan-1-ol
2: 92 percent / butan-1-ol / 70 °C
View Scheme
Multi-step reaction with 2 steps
1: 4-methyl-2-pentanone / 12 h / Reflux
2: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: acetic acid / 2 h / 90 - 95 °C
1.2: 12 h / Reflux
2.1: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: butan-1-ol / 9 h / 120 °C / Large scale
2: hydrogen / methanol / 45 h / 3102.97 Torr
View Scheme
Multi-step reaction with 2 steps
1: butan-1-ol / 9 h / 120 °C
2: hydrogen / methanol / 45 h / 25 °C / 3102.97 Torr
View Scheme
(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

(E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41.3 percent / sodium hydroxide / propan-2-ol / 8 h / Heating
2: 60.9 percent / H2 / palladium on charcoal / tetrahydrofuran / 21 h / 750.06 Torr / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: NaOH / propan-2-ol / Heating
2: H2 / 5percent Pd-C / tetrahydrofuran / 750.06 Torr / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / butan-1-ol / 4 h / 120 °C / Reflux
2: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 15 h / 120 °C / Inert atmosphere; Reflux
3: iron(III) chloride; hydrazine hydrate / methanol / 6 h / 80 °C / Reflux
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / butan-1-ol / 20 h / Reflux; Inert atmosphere
2: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 24 h / 100 °C / Inert atmosphere
3: palladium on carbon; hydrogen / methanol / 760.05 Torr
View Scheme
Multi-step reaction with 4 steps
1.1: sodium methylate / ethanol; methanol / 6 h / 78 °C / Inert atmosphere; Molecular sieve
1.2: 0.5 h / 20 °C
2.1: sodium tungstate; dihydrogen peroxide / acetone / 10 h / 40 °C
3.1: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere
4.1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr
View Scheme
palladium
7440-05-3

palladium

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine
152460-09-8

N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
In ethyl acetate
In ethyl acetate
6-chloro-N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidin-amine
1016637-24-3

6-chloro-N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidin-amine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With hydrogen; triethylamine; 5%-palladium/activated carbon In ethanol at 20℃; under 3750.38 Torr; for 40h; Product distribution / selectivity;
With hydrogen; triethylamine; 5% Pd(II)/C(eggshell) In ethanol at 20℃; under 3750.38 Torr; for 40h; Autoclave;
1-(5-amino-2-methylphenyl)-3-[3-oxo-3-(3-pyridinyl)-1-prop-1-enyl]guanidine
1026747-16-9

1-(5-amino-2-methylphenyl)-3-[3-oxo-3-(3-pyridinyl)-1-prop-1-enyl]guanidine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
With potassium hydroxide In butan-1-ol for 18h; Product distribution / selectivity; Heating / reflux;
β-oxo-3-pyridinepropanal sodium salt
39883-42-6, 41403-76-3

β-oxo-3-pyridinepropanal sodium salt

(2-methyl-5-aminophenyl)guanidine
581076-64-4

(2-methyl-5-aminophenyl)guanidine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Stage #1: β-oxo-3-pyridinepropanal sodium salt; (2-methyl-5-aminophenyl)guanidine With acetic acid In butan-1-ol at 20℃; for 1h; Inert atmosphere;
Stage #2: With potassium hydroxide In butan-1-ol for 18h; Reflux; Inert atmosphere;
(2-methyl-5-nitrophenyl)guanidine nitrate

(2-methyl-5-nitrophenyl)guanidine nitrate

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / water
2: 4-methyl-2-pentanone / 12 h / Reflux
3: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water
2.1: acetic acid / 2 h / 90 - 95 °C
2.2: 12 h / Reflux
3.1: hydrazine hydrate / palladium 10% on activated carbon / methanol / 8 h / 25 °C / Reflux; Inert atmosphere
View Scheme
2-(methylsulfanyl)-4-(3-pyridyl)pyrimidine

2-(methylsulfanyl)-4-(3-pyridyl)pyrimidine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C
2: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C
3: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C
2: potassium carbonate / N,N-dimethyl-formamide / 80 °C
3: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium tungstate; dihydrogen peroxide / acetone / 10 h / 40 °C
2: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere
3: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr
View Scheme
2-(methylsulfonyl)-4-(pyridin-3-yl)pyrimidine

2-(methylsulfonyl)-4-(pyridin-3-yl)pyrimidine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C
2: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 80 °C
2: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere
2: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr
View Scheme
4-(pyridin-3-yl)pyrimidine-2-thiol

4-(pyridin-3-yl)pyrimidine-2-thiol

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water
1.2: 20 °C
2.1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C
4.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water
1.2: 20 °C
2.1: sodium tungstate monohydrate; water; dihydrogen peroxide / acetone / 10 h / 40 °C
3.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C
4.1: iron(III) chloride hexahydrate; hydrazine hydrate / methanol / 6 h / 78 °C
View Scheme
Multi-step reaction with 4 steps
1: 0.5 h / 20 °C
2: sodium tungstate; dihydrogen peroxide / acetone / 10 h / 40 °C
3: triethylamine / 2-methyltetrahydrofuran / 5 h / 20 °C / Inert atmosphere
4: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / 20 °C / 1520.1 Torr
View Scheme
2-bromo-4-nitrotoluene
7745-93-9

2-bromo-4-nitrotoluene

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 15 h / 120 °C / Inert atmosphere; Reflux
2: iron(III) chloride; hydrazine hydrate / methanol / 6 h / 80 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 20 h / 20 - 100 °C / Inert atmosphere; Schlenk technique
2: hydrazine hydrate; iron(III) chloride; pyrographite / water / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium iodide; potassium carbonate / 1,4-dioxane / Inert atmosphere; Reflux
2: ammonium formate; palladium 10% on activated carbon / methanol / 4 h / 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation
2: zinc; ammonium chloride / tetrahydrofuran / 0.17 h / 80 °C / Microwave irradiation
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 24 h / 120 °C / Inert atmosphere
2: palladium on activated charcoal; hydrogen / ethyl acetate / Inert atmosphere
View Scheme
4-pyridin-3-ylpyrimidin-2-ylamine
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 15 h / 120 °C / Inert atmosphere; Reflux
2: iron(III) chloride; hydrazine hydrate / methanol / 6 h / 80 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium tert-butylate / dimethyl sulfoxide / 12 h / 120 °C
2: tin(ll) chloride; hydrogenchloride / methanol / 10 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 20 h / 20 - 100 °C / Inert atmosphere; Schlenk technique
2: hydrazine hydrate; iron(III) chloride; pyrographite / water / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide / dimethyl sulfoxide; water / 10 h / 100 °C
2: potassium tert-butylate / dimethyl sulfoxide / 12 h / 120 °C
3: tin(ll) chloride; hydrogenchloride / methanol / 10 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 12 h / 85 °C / Inert atmosphere
2.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 100 °C / Inert atmosphere
3.1: sodium hydroxide; water / ethanol / 5 h / 100 °C
4.1: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C
4.2: 100 °C
View Scheme
Multi-step reaction with 5 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 12 h / 85 °C / Inert atmosphere
2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 100 °C / Inert atmosphere
3: sodium hydroxide; water / ethanol / 5 h / 100 °C
4: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C
5: trifluoroacetic acid / dichloromethane / 8 h
View Scheme
1-methyl-4-nitrobenzene
99-99-0

1-methyl-4-nitrobenzene

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: bromine; iron / 1.5 h / 80 °C / Inert atmosphere; Schlenk technique
2: copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 20 h / 20 - 100 °C / Inert atmosphere; Schlenk technique
3: hydrazine hydrate; iron(III) chloride; pyrographite / water / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; N-Bromosuccinimide / water
2: copper(l) iodide; potassium iodide; potassium carbonate / 1,4-dioxane / Inert atmosphere; Reflux
3: ammonium formate; palladium 10% on activated carbon / methanol / 4 h / 30 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 4-pyridin-3-ylpyrimidin-2-ylamine; iron; bromine / 80 °C
2: copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 0.5 h / 120 °C / Microwave irradiation
3: zinc; ammonium chloride / tetrahydrofuran / 0.17 h / 80 °C / Microwave irradiation
View Scheme
N-(4,5-dimethoxy-2-nitrobenzyl)-N-(4-methyl-3-((4-(pyridine-3-yl)pyrimidine-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide

N-(4,5-dimethoxy-2-nitrobenzyl)-N-(4-methyl-3-((4-(pyridine-3-yl)pyrimidine-2-yl)amino)phenyl)-4-((4-methylpiperazin-1-yl)methyl)benzamide

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 0.17 h / Irradiation
2: hydrogenchloride; acetic acid / 20 °C / Reflux
View Scheme
N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride
1207534-99-3

N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / isopropyl alcohol / 24 h / Reflux
2: hydrogen; platinum(IV) oxide / tetrahydrofuran / 1.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / propan-1-ol / 24 h / Reflux
2: platinum(IV) oxide; hydrogen
View Scheme
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

3-Iodobenzoic acid
618-51-9

3-Iodobenzoic acid

C23H18IN5O

C23H18IN5O

Conditions
ConditionsYield
Stage #1: 3-Iodobenzoic acid With thionyl chloride; N,N-dimethyl-formamide In N,N-dimethyl-formamide at 20℃; for 17h;
Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2.5h;
100%
1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C22H31N5Si2

C22H31N5Si2

Conditions
ConditionsYield
With hydroxylamine hydrochloride for 5h; Reflux;99.6%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C22H31N5Si2

C22H31N5Si2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Solvent;99.6%
4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride

4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

imatinib
152459-95-5

imatinib

Conditions
ConditionsYield
Stage #1: 4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride; 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In water at 0℃;
Stage #2: With sodium hydroxide In water at 50 - 55℃; pH=9 - 9.5; Product distribution / selectivity;
99.26%
With pyridine at 0 - 20℃; for 1h; Product distribution / selectivity;95%
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With pyridine for 0.333333h; Autoclave;
Stage #2: 4-((4-methylpiperazin-1-yl)methyl)benzoyl chloride dihydrochloride at 0 - 25℃; for 8h;
92.7%
trimethylsilyl bromide
2857-97-8

trimethylsilyl bromide

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C22H31N5Si2

C22H31N5Si2

Conditions
ConditionsYield
With triethylamine In 2-methyltetrahydrofuran at 0 - 20℃;99.2%
p-(chloromethyl)benzoyl chloride
876-08-4

p-(chloromethyl)benzoyl chloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide
404844-11-7

4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 4h;99%
With triethylamine In tetrahydrofuran at 0℃; for 1h; Large scale;98.1%
With triethylamine In tetrahydrofuran at 0℃; for 4h;97.4%
p-(chloromethyl)benzoyl chloride
876-08-4

p-(chloromethyl)benzoyl chloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

4-(сhloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide hydrochloride
404844-10-6

4-(сhloromethyl)-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]-benzamide hydrochloride

Conditions
ConditionsYield
In 1,4-dioxane at 22 - 34℃; for 2.75h;99%
C17H23N4O(1+)*CF3O3S(1-)

C17H23N4O(1+)*CF3O3S(1-)

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

imatinib
152459-95-5

imatinib

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 40 - 50℃; for 6h; Time;97.8%
benzoyl chloride
98-88-4

benzoyl chloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

N-(4-methyl-3(4-(pyridine-3-yl)pyrimidin-2-ylamino)phenyl)benzamide
152459-94-4

N-(4-methyl-3(4-(pyridine-3-yl)pyrimidin-2-ylamino)phenyl)benzamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 25℃; for 3h;97%
With pyridine for 23h; Ambient temperature;18.3%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

diethyl ((4-(dimethylamino)phenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

diethyl ((4-(dimethylamino)phenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.25h; Reagent/catalyst; Microwave irradiation;96.2%
indole-2,3-dione
91-56-5

indole-2,3-dione

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

3-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)imino)indolin-2-one

3-((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)imino)indolin-2-one

Conditions
ConditionsYield
In toluene for 24h; Dean-Stark; Reflux;96%
4-[(4-methylpiperazin-1-yl)methyl]bromobenzene
368879-17-8

4-[(4-methylpiperazin-1-yl)methyl]bromobenzene

carbon monoxide
201230-82-2

carbon monoxide

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

imatinib
152459-95-5

imatinib

Conditions
ConditionsYield
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 50℃; under 760.051 Torr; for 36h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;95.8%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

diethyl ((4-hydroxyphenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

diethyl ((4-hydroxyphenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.266667h; Microwave irradiation;95.8%
4-Diethylaminobenzaldehyde
120-21-8

4-Diethylaminobenzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

diethyl ((4-(diethylamino)phenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

diethyl ((4-(diethylamino)phenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.266667h; Microwave irradiation;95.7%
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

N-(5-azido-2-methylphenyl)-4-(pyridine-3-yl)pyrimidin-2-amine
1346617-84-2

N-(5-azido-2-methylphenyl)-4-(pyridine-3-yl)pyrimidin-2-amine

Conditions
ConditionsYield
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.5h;
Stage #2: With sodium azide In water at 0 - 5℃; for 3h;
95%
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;85%
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With sodium azide In water at 0 - 20℃; for 3h;
81%
Stage #1: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h;
Stage #2: With sodium azide In water at 0℃; for 2h;
With hydrogenchloride; sodium azide; sodium nitrite In water at 0℃; for 3h;
succinic acid anhydride
108-30-5

succinic acid anhydride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C20H19N5O3
1450754-50-3

C20H19N5O3

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;95%
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)thiourea

N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)thiourea

Conditions
ConditionsYield
Stage #1: ammonium thiocyanate With benzoyl chloride In acetone for 0.0833333h; Reflux;
Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In acetone Reflux;
95%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

diethyl ((3,4,5-trimethoxyphenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

diethyl ((3,4,5-trimethoxyphenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.25h; Microwave irradiation;94.4%
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

3-chlorobenzoate
535-80-8

3-chlorobenzoate

3-chloro-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

3-chloro-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 20℃; for 1h;94%
2-[(tert-butoxy)carbonyl]-1 ,2,3,4-tetrahydroisoquinoline-7-carboxylic acid
149353-95-7

2-[(tert-butoxy)carbonyl]-1 ,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

C31H32N6O3

C31H32N6O3

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h;94%
4-(N,N-Dimethylaminocarbonyl)benzoic acid
34231-49-7

4-(N,N-Dimethylaminocarbonyl)benzoic acid

trifluoroacetic acid
76-05-1

trifluoroacetic acid

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

N1,N1-dimethyl-N4-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzene-1,4-dicarboxamide trifluoroacetate salt

N1,N1-dimethyl-N4-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)benzene-1,4-dicarboxamide trifluoroacetate salt

Conditions
ConditionsYield
Stage #1: 4-(N,N-Dimethylaminocarbonyl)benzoic acid; 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: trifluoroacetic acid In water; acetonitrile
94%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

diethyl ((4-chlorophenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

diethyl ((4-chlorophenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.283333h; Microwave irradiation;93.8%
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

3,5-dinitrobenoyl chloride
99-33-2

3,5-dinitrobenoyl chloride

N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]-3,5-dinitrobenzamide
1207534-76-6

N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]-3,5-dinitrobenzamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃;93%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

diethyl ((3-nitrophenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

diethyl ((3-nitrophenyl)((4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)amino)methyl)phosphonate

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.3h; Microwave irradiation;92.6%
6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

4-((4-methylpiperazin-1-yl)methyl)benzoic acid dihydrochloride

4-((4-methylpiperazin-1-yl)methyl)benzoic acid dihydrochloride

imatinib
152459-95-5

imatinib

Conditions
ConditionsYield
Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With pyridine; thionyl chloride at 50 - 60℃; for 3h;
Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine at -10 - 0℃; for 1h;
92.5%
Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 50℃; for 2h;
Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine In N,N-dimethyl-formamide at 70℃; for 12h;
91%
Stage #1: 4-[(4-methylpiperazin-1-yl)methyl]benzoic acid dihydrochloride With pyridine; thionyl chloride at 20 - 50℃; for 1 - 2h;
Stage #2: 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine With pyridine at 0 - 25℃; for 1h; Product distribution / selectivity;
90%
4-nitro-3-(trifluoromethyl)benzoyl chloride
98187-16-7

4-nitro-3-(trifluoromethyl)benzoyl chloride

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]-4-nitro-3-trifluoromethylbenzamide
945028-63-7

N-[4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]-4-nitro-3-trifluoromethylbenzamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃;92%
With pyridine In dichloromethane at 0℃;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 26h;
With triethylamine In tetrahydrofuran

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