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329974-09-6

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329974-09-6 Usage

Chemical Properties

Off-white solid

Uses

4-?Bromo-?2,?6-?diaminopyridine is a versatile reactant used in the preparation of a uracil DNA glycosylase which is a DNA repair enzyme with selective recognition of uracil and its derivatives.

Check Digit Verification of cas no

The CAS Registry Mumber 329974-09-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,2,9,9,7 and 4 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 329974-09:
(8*3)+(7*2)+(6*9)+(5*9)+(4*7)+(3*4)+(2*0)+(1*9)=186
186 % 10 = 6
So 329974-09-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H6BrN3/c6-3-1-4(7)9-5(8)2-3/h1-2H,(H4,7,8,9)

329974-09-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-bromopyridine-2,6-diamine

1.2 Other means of identification

Product number -
Other names 2.6-diamino-4-bromopyridine

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:329974-09-6 SDS

329974-09-6Synthetic route

(4-bromo-6-tert-butoxycarbonylamino-pyridin-2-yl)-carbamic acid tert-butyl ester
410534-47-3

(4-bromo-6-tert-butoxycarbonylamino-pyridin-2-yl)-carbamic acid tert-butyl ester

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane74%
With trifluoroacetic acid In toluene for 2h; Reflux;209 mg
4-bromo-pyridine-2,6-dicarbonyl diazide
329974-10-9

4-bromo-pyridine-2,6-dicarbonyl diazide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Stage #1: 4-bromo-pyridine-2,6-dicarbonyl diazide With tert-butyl alcohol Heating;
Stage #2: With trifluoroacetic acid In dichloromethane
74%
N,N'-dibenzyl-4-bromo-1-oxypyridine-2,6-diamine

N,N'-dibenzyl-4-bromo-1-oxypyridine-2,6-diamine

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
With sulfuric acid at 40℃; for 1.5h;68.5%
sodium hydroxide
1310-73-2

sodium hydroxide

trifluoroacetic acid
76-05-1

trifluoroacetic acid

4-bromo-pyridine-2,6-dicarbonyl diazide
329974-10-9

4-bromo-pyridine-2,6-dicarbonyl diazide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Stage #1: 4-bromo-pyridine-2,6-dicarbonyl diazide In toluene; tert-butyl alcohol for 12h; Heating / reflux;
Stage #2: trifluoroacetic acid In toluene for 2h; Heating / reflux;
Stage #3: sodium hydroxide In diethyl ether; water
67%
4-bromo-1-oxypyridine-2,6-diamine

4-bromo-1-oxypyridine-2,6-diamine

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
With iron; acetic acid In water at 100℃; for 2h;59.4%
2,4,6-tribromopyridine
2408-70-0

2,4,6-tribromopyridine

A

4-amino-2,6-dibromopyridine
39771-34-1

4-amino-2,6-dibromopyridine

B

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

C

2,4-diamino-6-bromopyridine

2,4-diamino-6-bromopyridine

Conditions
ConditionsYield
With ammonia In waterA n/a
B 25%
C n/a
2,4,6-tribromopyridine
2408-70-0

2,4,6-tribromopyridine

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
With ammonium hydroxide at 200℃;
4-bromopyridine-2,6-biscarbonamide
668992-72-1

4-bromopyridine-2,6-biscarbonamide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
With potassium hydroxide; bromine for 4h; Hofmann rearrangement; Heating;
With bromine; potassium hydroxide at 0 - 90℃; for 2.5h;
C5H4BrClN2
1206250-19-2

C5H4BrClN2

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
With ammonia
2,6-Dibromopyridine
626-05-1

2,6-Dibromopyridine

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale
2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
4: toluene / 2 h / 70 °C
5: sulfuric acid / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 5 steps
1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale
2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
4: potassium carbonate / toluene / 21 h / 110 °C
5: sulfuric acid / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 5 steps
1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale
2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
4: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube
5: iron; acetic acid / water / 2 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1: trifluoroacetic acid; dihydrogen peroxide / water / 5 h / 95 - 100 °C / Large scale
2: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
3: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
4: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube
5: iron; acetic acid / water / 2 h / 100 °C
View Scheme
2,6-dibromopyridin N-oxide
25373-69-7

2,6-dibromopyridin N-oxide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
3: toluene / 2 h / 70 °C
4: sulfuric acid / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
3: potassium carbonate / toluene / 21 h / 110 °C
4: sulfuric acid / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 4 steps
1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
3: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube
4: iron; acetic acid / water / 2 h / 100 °C
View Scheme
Multi-step reaction with 4 steps
1: sulfuric acid; nitric acid / 20 h / 60 °C / Large scale
2: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
3: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube
4: iron; acetic acid / water / 2 h / 100 °C
View Scheme
2,6-dibromo-4-nitro-pyridine 1-oxide
98027-81-7

2,6-dibromo-4-nitro-pyridine 1-oxide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
2: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube
3: iron; acetic acid / water / 2 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
2: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube
3: iron; acetic acid / water / 2 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
2: toluene / 2 h / 70 °C
3: sulfuric acid / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: Acetyl bromide / acetic acid / 5 h / 60 - 80 °C
2: potassium carbonate / toluene / 21 h / 110 °C
3: sulfuric acid / 1.5 h / 40 °C
View Scheme
2,4,6-tribromopyridine-1-oxide hydrobromide

2,4,6-tribromopyridine-1-oxide hydrobromide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium hydroxide / water / 3 h / 110 °C / Sealed tube
2: iron; acetic acid / water / 2 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: ammonium hydroxide / water / 5 h / 140 °C / Sealed tube
2: iron; acetic acid / water / 2 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / toluene / 21 h / 110 °C
2: sulfuric acid / 1.5 h / 40 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene / 2 h / 70 °C
2: sulfuric acid / 1.5 h / 40 °C
View Scheme
chelidamic acid
138-60-3

chelidamic acid

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: phosphorus pentabromide / 3 h / 80 °C
1.2: 1 h / -10 °C
2.1: ammonia / methanol / 2 h / 20 °C
3.1: bromine; potassium hydroxide / 2.5 h / 0 - 90 °C
View Scheme
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

4-chloro-aniline
106-47-8

4-chloro-aniline

(E)-4-bromo-3-((4-chlorophenyl)diazenyl)pyridine-2,6-diamine

(E)-4-bromo-3-((4-chlorophenyl)diazenyl)pyridine-2,6-diamine

Conditions
ConditionsYield
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: 4-bromo-pyridine-2,6-diamine In water for 1.5h;
99%
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃;
Stage #2: 4-bromo-pyridine-2,6-diamine In water for 1.5h;
99%
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: 4-bromo-pyridine-2,6-diamine With urea In water for 1.5h;
Stage #3: With sodium acetate In water
99%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

n-valeryl chloride
638-29-9

n-valeryl chloride

2,6-di-n-butylamino-4-bromo-pyridine
662164-82-1

2,6-di-n-butylamino-4-bromo-pyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane for 1.5h;97%
With triethylamine In dichloromethane at 20℃; for 1.5h;69.2%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

acetyl chloride
75-36-5

acetyl chloride

N,N'-(4-bromo-2,6-pyridinediyl)bisacetamide
662164-81-0

N,N'-(4-bromo-2,6-pyridinediyl)bisacetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 25h; Inert atmosphere;97%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

butyryl chloride
141-75-3

butyryl chloride

N,N'-(4-bromopyridine-2,6-diyl)dibutyramide

N,N'-(4-bromopyridine-2,6-diyl)dibutyramide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;95%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

propionyl chloride
79-03-8

propionyl chloride

4-bromo-2,6-dipropamidopyridine

4-bromo-2,6-dipropamidopyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane90%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

7-bromo-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine
329972-51-2

7-bromo-2-pyridin-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine79%
With potassium hydroxide; mesitylenesulfonylhydroxylamine
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

ethyl Bromopyruvate
70-23-5

ethyl Bromopyruvate

ethyl 5-amino-7-bromo-imidazo[1,2-a]pyridine-2-carboxylate
865604-77-9

ethyl 5-amino-7-bromo-imidazo[1,2-a]pyridine-2-carboxylate

Conditions
ConditionsYield
In ethanol for 3h; Heating / reflux;75%
In ethanol for 5h; Reflux;
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

N,N'-(4-bromopyridine-2,6-diyl)bis(2-methylpropanamide)

N,N'-(4-bromopyridine-2,6-diyl)bis(2-methylpropanamide)

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Reflux;75%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

(Z)-1-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolan-2’-yl)-1,2-diphenylethene
264144-59-4

(Z)-1-(4',4',5',5'-tetramethyl-1’,3’,2’-dioxaborolan-2’-yl)-1,2-diphenylethene

(E)-4-(1,2-diphenylvinyl)pyridine-2,6-diamine

(E)-4-(1,2-diphenylvinyl)pyridine-2,6-diamine

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane at 70℃; for 16h;75%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

acetic anhydride
108-24-7

acetic anhydride

N,N'-(4-bromo-2,6-pyridinediyl)bisacetamide
662164-81-0

N,N'-(4-bromo-2,6-pyridinediyl)bisacetamide

Conditions
ConditionsYield
In pyridine at 20℃; for 10h;68%
With pyridine at 20℃; for 10h;68%
With pyridine68%
With pyridine at 20℃; Inert atmosphere;61%
Stage #1: 4-bromo-pyridine-2,6-diamine; acetic anhydride With sulfuric acid In water for 72h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In water
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

3,3-dimethylbutanoic acid chloride
7065-46-5

3,3-dimethylbutanoic acid chloride

N-(6-amino-4-bromopyridin-2-yl)-3,3-dimethylbutanamide

N-(6-amino-4-bromopyridin-2-yl)-3,3-dimethylbutanamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h;68%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

(S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid
13734-31-1

(S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid

tert-butyl N-{1-[(6-amino-4-bromopyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate

tert-butyl N-{1-[(6-amino-4-bromopyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate

Conditions
ConditionsYield
Stage #1: (S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice;
Stage #2: 4-bromo-pyridine-2,6-diamine In 1-methyl-pyrrolidin-2-one; dichloromethane at 20℃; for 72h;
67%
Stage #1: (S)-N-tert-butoxycarbonyl-N-methyl-2-amino-propionic acid With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; Cooling with ice;
Stage #2: 4-bromo-pyridine-2,6-diamine In 1-methyl-pyrrolidin-2-one; dichloromethane at 20℃; for 72h;
67%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

3-methoxycarbonylbenzyl bromide
1129-28-8

3-methoxycarbonylbenzyl bromide

methyl 3-((2,6-diaminopyridin-4-yl)methyl)benzoate

methyl 3-((2,6-diaminopyridin-4-yl)methyl)benzoate

Conditions
ConditionsYield
Stage #1: 3-methoxycarbonylbenzyl bromide With chloro-trimethyl-silane; zinc In tetrahydrofuran; ethylene dibromide at 20℃; for 1h; Negishi Coupling; Inert atmosphere;
Stage #2: 4-bromo-pyridine-2,6-diamine With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate at 20℃; Negishi Coupling;
63.9%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

1-bromomethyl-3-chlorobenzene
766-80-3

1-bromomethyl-3-chlorobenzene

4-(3-chlorobenzyl)pyridine-2,6-diamine

4-(3-chlorobenzyl)pyridine-2,6-diamine

Conditions
ConditionsYield
Stage #1: 1-bromomethyl-3-chlorobenzene With chloro-trimethyl-silane; zinc In tetrahydrofuran; ethylene dibromide at 20℃; for 0.5h; Negishi Coupling; Inert atmosphere;
Stage #2: 4-bromo-pyridine-2,6-diamine With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate at 20℃;
58.6%
2-methoxythiophene-5-carbaldehyde
35087-46-8

2-methoxythiophene-5-carbaldehyde

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

7-bromo-2-(5-methoxythiophen-2-yl)[1,2,4]triazolo[1,5-a]pyridin-5-ylamine
329972-48-7

7-bromo-2-(5-methoxythiophen-2-yl)[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine56%
With potassium hydroxide; mesitylenesulfonylhydroxylamine
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

3,4-dichlophenylboronic acid
151169-75-4

3,4-dichlophenylboronic acid

4-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine
329974-12-1

4-(3,4-Dichloro-phenyl)-pyridine-2,6-diamine

Conditions
ConditionsYield
With sodium carbonate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) In 1,2-dimethoxyethane at 80℃; for 17h;52%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

benzyl bromide
100-39-0

benzyl bromide

4-bromo-N,N,N',N'-tetrabenzyl-2,6-diaminopyridine
1204589-47-8

4-bromo-N,N,N',N'-tetrabenzyl-2,6-diaminopyridine

Conditions
ConditionsYield
Stage #1: 4-bromo-pyridine-2,6-diamine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h;
Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
47%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
214360-67-5

2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-(3,4,5-trimethoxyphenyl)pyridine-2,6-diamine hydrochloride
1309365-48-7

4-(3,4,5-trimethoxyphenyl)pyridine-2,6-diamine hydrochloride

Conditions
ConditionsYield
Stage #1: 4-bromo-pyridine-2,6-diamine; 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane With caesium carbonate In methanol at 100℃; for 18h; Suzuki coupling; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol
44%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

di-tert-butyl (4-bromopyridine-2,6-diyl)bis((tert-butoxycarbonyl)carbamate)

di-tert-butyl (4-bromopyridine-2,6-diyl)bis((tert-butoxycarbonyl)carbamate)

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 70℃; Inert atmosphere;43%
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

benzaldehyde
100-52-7

benzaldehyde

7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine
329974-11-0

7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine39%
potassium hydroxide
1310-58-3

potassium hydroxide

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

benzaldehyde
100-52-7

benzaldehyde

7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine
329974-11-0

7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
Stage #1: 4-bromo-pyridine-2,6-diamine With mesitylenesulfonylhydroxylamine In methanol at -5℃; for 0.25h;
Stage #2: benzaldehyde In methanol for 0.5h;
Stage #3: potassium hydroxide
39%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

7-bromo-2-thiophen-2-yl[1,2,4]triazolo[1,5-a]pyridin-5-ylamine
329972-33-0

7-bromo-2-thiophen-2-yl[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine37%
With potassium hydroxide; mesitylenesulfonylhydroxylamine
furfural
98-01-1

furfural

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

7-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine
329972-27-2

7-bromo-2-furan-2-yl-[1,2,4]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine36%
With potassium hydroxide; mesitylenesulfonylhydroxylamine
5-Methylfurfural
620-02-0

5-Methylfurfural

4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

7-bromo-2-(5-methylfuran-2-yl)[1,2,4 ]triazolo[1,5-a]pyridin-5-ylamine
329972-28-3

7-bromo-2-(5-methylfuran-2-yl)[1,2,4 ]triazolo[1,5-a]pyridin-5-ylamine

Conditions
ConditionsYield
With potassium hydroxide; air; mesitylenesulfonylhydroxylamine35%
With potassium hydroxide; mesitylenesulfonylhydroxylamine
4-bromo-pyridine-2,6-diamine
329974-09-6

4-bromo-pyridine-2,6-diamine

2,2-difluoroethyl triflate
74427-22-8

2,2-difluoroethyl triflate

4-bromo-N-(2,2-difluoro-ethyl)-pyridine-2,6-diamine
1158784-72-5

4-bromo-N-(2,2-difluoro-ethyl)-pyridine-2,6-diamine

Conditions
ConditionsYield
Stage #1: 4-bromo-pyridine-2,6-diamine With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h;
Stage #2: 2,2-difluoroethyl triflate In tetrahydrofuran at 25℃; for 18h;
32%

329974-09-6Relevant articles and documents

HETEROARYLAMINOISOQUINOLINES, METHODS FOR THEIR PREPARATION AND THERAPEUTIC USES THEREOF

-

, (2016/08/23)

The application is directed to compounds of formula (IA) : and specifically compounds of formula (I) and their salts and solvates, wherein R1, R11, R12, R13, R4, R5, n, A1, A2, and A3 are as set forth in the specification, as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of conditions associated with the alteration of the activity of β-galactosidase, specially galactosidase beta-1 or GLB1, including GM1 gangliosidoses and Morquio syndrome, type B.

Lead generation: Sowing the seeds for future success

Bleicher, Konrad H.,Nettekoven, Matthias,Peters, Jens-Uwe,Wyler, Rene

, p. 588 - 600 (2007/10/03)

Lead generation and the associated hit-to-lead process are key strategic elements in modern pharmaceutical research, and most companies have implemented this concept. Efficient lead generation is one of the main attempts to reduce the high attrition rates observed along the drug discovery process by focussing on the early developmental phases. The level of integration of the lead generation activities within the discovery organization, the flexibility in assessing and implementing new chemistries and new technologies, the high-quality standards set for the identification of the best possible chemical lead series will ultimately determine the future success in discovering new medicines.

The development of a practical and reliable large-scale synthesis of 2,6-diamino-4-bromopyridine

Nettekoven, Matthias,Jenny, Christian

, p. 38 - 43 (2013/09/05)

A novel, safer, and efficient synthetic route to 2,6-diamino-4-bromopyridine has been developed. In discovery research a five-step synthesis afforded 2,6-diamino-4-bromopyridine in 56% yield with a double Curtius rearrangement as a key transformation. Due to potential safety concerns on larger scale an alternative synthetic strategy was necessary. Starting from 2,4-dibromopyridine-N-oxide two complementary procedures have been developed to access 2,6-diamino-4-bromopyridine. The four-step procedure yielded in 28% overall, and the five-step procedure, in 33% overall 2,6-diamino-4-bromopyridine in a safe and straightforward manner using a regioselective 2,6-diamination reaction as key step. Additionally, a general route to unsymmetrical substituted pyridine N-oxide derivatives is disclosed.

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