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152460-10-1

Basic Information
CAS No.: 152460-10-1
Name: N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
Molecular Structure:
Molecular Structure of 152460-10-1 (N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine)
Formula: C16H15N5
Molecular Weight: 277.32
Synonyms: 4-Methyl-3-[4-(3-pyridyl)pyrimidin-2-ylamino]aniline;4-Methyl-N'-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine;
EINECS: 1806241-263-5
Density: 1.266 g/cm3
Melting Point: 133-135 °C
Boiling Point: 537.325 °C at 760 mmHg
Flash Point: 278.765 °C
Solubility:
Appearance: yellow solid
Hazard Symbols: Xn,Xi
Risk Codes: R36/37/38; R22
Safety:
Transport Information:
PSA: 76.72000
LogP: 3.82700
Synthetic route
152460-09-8

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

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%
152459-95-5

imatinib

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

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%
55314-16-4, 75415-01-9, 123367-26-0

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

581076-64-4

(2-methyl-5-aminophenyl)guanidine

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%
7745-93-9

2-bromo-4-nitrotoluene

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

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%
7803-57-8

hydrazine hydrate

152460-09-8

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

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

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%
641569-94-0

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

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

152460-09-8

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

152460-10-1

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

Conditions
ConditionsYield
In hydrogenchloride46%
350-03-8

methyl-3-pyridylketone

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
55314-16-4, 75415-01-9, 123367-26-0

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

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

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
99-55-8

2-methyl-5-nitroaniline

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
152460-07-6

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

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
55314-16-4, 75415-01-9, 123367-26-0

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

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
7440-05-3

palladium

152460-09-8

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

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
1016637-24-3

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

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;
1026747-16-9

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

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;
39883-42-6, 41403-76-3

β-oxo-3-pyridinepropanal sodium salt

581076-64-4

(2-methyl-5-aminophenyl)guanidine

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

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

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

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

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
7745-93-9

2-bromo-4-nitrotoluene

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
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

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
1692-25-7

3-pyridylboronic acid

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
99-99-0

1-methyl-4-nitrobenzene

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

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
1207534-99-3

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

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
152460-10-1

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

618-51-9

3-Iodobenzoic acid

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%
999-97-3

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

152460-10-1

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

C22H31N5Si2

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

chloro-trimethyl-silane

152460-10-1

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

C22H31N5Si2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Solvent;99.6%

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

152460-10-1

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

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%
2857-97-8

trimethylsilyl bromide

152460-10-1

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

C22H31N5Si2

Conditions
ConditionsYield
With triethylamine In 2-methyltetrahydrofuran at 0 - 20℃;99.2%
876-08-4

p-(chloromethyl)benzoyl chloride

152460-10-1

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

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%
876-08-4

p-(chloromethyl)benzoyl chloride

152460-10-1

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

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-)

152460-10-1

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

152459-95-5

imatinib

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

benzoyl chloride

152460-10-1

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

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%
762-04-9

phosphonic acid diethyl ester

100-10-7

4-dimethylamino-benzaldehyde

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

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

indole-2,3-dione

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

Conditions
ConditionsYield
In toluene for 24h; Dean-Stark; Reflux;96%
368879-17-8

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

201230-82-2

carbon monoxide

152460-10-1

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

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%
123-08-0

4-hydroxy-benzaldehyde

762-04-9

phosphonic acid diethyl ester

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

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

4-Diethylaminobenzaldehyde

762-04-9

phosphonic acid diethyl ester

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

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.266667h; Microwave irradiation;95.7%
152460-10-1

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

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;
108-30-5

succinic acid anhydride

152460-10-1

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

1450754-50-3

C20H19N5O3

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

ammonium thiocyanate

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

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%
86-81-7

3,4,5-trimethoxy-benzaldehyde

762-04-9

phosphonic acid diethyl ester

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

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.25h; Microwave irradiation;94.4%
152460-10-1

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

535-80-8

3-chlorobenzoate

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%
149353-95-7

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

152460-10-1

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

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%
34231-49-7

4-(N,N-Dimethylaminocarbonyl)benzoic acid

76-05-1

trifluoroacetic acid

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

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%
104-88-1

4-chlorobenzaldehyde

762-04-9

phosphonic acid diethyl ester

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

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.283333h; Microwave irradiation;93.8%
152460-10-1

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

99-33-2

3,5-dinitrobenoyl chloride

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%
99-61-6

3-nitro-benzaldehyde

762-04-9

phosphonic acid diethyl ester

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

Conditions
ConditionsYield
With nickel(II) oxide In neat (no solvent) for 0.3h; Microwave irradiation;92.6%
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

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%
98187-16-7

4-nitro-3-(trifluoromethyl)benzoyl chloride

152460-10-1

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

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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404844-11-7
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    Alias: N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine; 4-Methyl-N'-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine; N-(5-amino-2-methylphenyl)-4-(3-pyrdyl)-2-pydimidineamine; N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine

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    N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine Basic information Product Name: N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine Synonyms: IMatinib IMpurity C;N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine 4-Met

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Specification

The N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine, with the CAS registry number 152460-10-1,is also known as Oleylamine, ethoxylated. It belongs to the product categories of Aromatics Compounds;Aromatics;Bases & Related Reagents;Inhibitors;Nucleotides. This chemical's molecular formula is C16H15N5 and molecular weight is 277.3237. What's more,Its systematic name is N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine. It is a yellow solid which is a selective inhibitor of protein kinase c

Physical properties about N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine are:
(1)ACD/LogP:1.68±0.46; (2)# of Rule of 5 Violations:0; (3)ACD/LogD (pH 5.5):1.63; (4)ACD/LogD (pH 7.4):1.68; (5)ACD/BCF (pH 5.5):9.82; (6)ACD/BCF (pH 7.4):11.11; (7)ACD/KOC (pH 5.5): 172.25; (8)ACD/KOC (pH 7.4): 194.96; (9)#H bond acceptors:5; (10)#H bond donors:3; (11)#Freely Rotating Bonds:3; (12)Index of Refraction:1.688; (13)Molar Refractivity:83.6±0.3 cm3; (14)Molar Volume:219.0±3.0 cm3; (15)Polarizability:33.1±0.5 10-24cm3; (16)Surface Tension:64.2±3.0 dyne/cm; (17)Density:1.3±0.1 g/cm3; (18)Flash Point:278.8±32.9 °C; (19)Enthalpy of Vaporization:81.4±3.0 kJ/mol; (20)Boiling Point:537.3±60.0 °C at 760 mmHg; (21)Vapour Pressure:0.0±1.4 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)N;
(2)Std. InChI:InChI=1S/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);
(3)Std. InChIKey:QGAIPGVQJVGBIA-UHFFFAOYSA-N.