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66521-66-2

Basic Information
CAS No.: 66521-66-2
Name: 2-Pyrimidinamine,4-(3-pyridinyl)-
Molecular Structure:
Molecular Structure of 66521-66-2 (2-Pyrimidinamine,4-(3-pyridinyl)-)
Formula: C9H8N4
Molecular Weight: 172.19
Synonyms: 4-(3-Pyridyl)-2-pyrimidinamine;4-(Pyridin-3-yl)pyrimidin-2-amine;
EINECS: 1312995-182-4
Density: 1.259 g/cm3
Melting Point: 189-191 °C
Boiling Point: 439.9 °C at 760 mmHg
Flash Point: 250 °C
Solubility:
Appearance:
Hazard Symbols: T
Risk Codes: 25-20/21/22
Safety: 45-36/37
Transport Information:
PSA: 64.69000
LogP: 1.70200
Synthetic route
506-93-4

guanidine nitrate

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

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
In butan-1-ol for 12h; Reflux;93%
With sodium hydroxide In butan-1-ol for 20h; Reflux; Inert atmosphere;76%
With sodium hydroxide In butan-1-ol for 24h; Reflux;4.49 g
50-01-1

guanidine hydrochloride

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

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl alcohol at 85℃;90%
With potassium carbonate In propan-1-ol Reflux; Inert atmosphere;87%
With sodium hydroxide In butan-1-ol Reflux;85%
483324-01-2

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With ammonium hydroxide In water at 80℃; for 16h; Sealed tube;87%
506-93-4

guanidine nitrate

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

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With sodium hydroxide In butan-1-ol for 12h; Inert atmosphere; Schlenk technique; Reflux;85.5%
With sodium hydroxide In butan-1-ol for 16h; Reflux;85%
With sodium hydroxide In butan-1-ol for 16h; Reflux;67%
With sodium hydroxide In butan-1-ol for 12h; Reflux;
With sodium hydroxide In butan-1-ol at 90℃; for 0.333333h; Microwave irradiation;1.18 g
3993-78-0

2-amino-4-chloropyrimidine

1692-25-7

3-pyridylboronic acid

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 100℃; for 6h; Inert atmosphere;81%
With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide In water; dimethyl sulfoxide at 100℃; for 10h; Suzuki Coupling;72%
55314-16-4, 75415-01-9, 123367-26-0

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With guanidine hydrochloride; sodium hydroxide In isopropyl alcohol for 12h; Reflux;75%
With guanidine hydrochloride; sodium hydroxide In isopropyl alcohol for 18h; Inert atmosphere; Reflux;65%
With guanidine hydrochloride; sodium ethanolate In ethanol for 8h; Heating;
Multi-step reaction with 2 steps
1.1: nitric acid / ethanol / 0 °C
1.2: Reflux
1.3: Reflux
2.1: PYRIMIDINE; hydrazine hydrate / methanol / 0.25 h / 50 - 60 °C
View Scheme
Multi-step reaction with 2 steps
1.1: nitric acid / ethanol / 0 °C
1.2: Reflux
1.3: Reflux
2.1: PYRIMIDINE; hydrazine hydrate / methanol / 0.25 h / 50 - 60 °C
View Scheme
50-01-1

guanidine hydrochloride

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

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With sodium ethanolate In ethanol for 6h; Heating;73%
With sodium hydroxide In butan-1-ol at 85℃; for 12h; Solvent;72%
With sodium hydroxide In butan-1-ol for 12h; Reflux;5.162 g
1392279-39-8

(Z)-3-chloro-3-(pyridin-3-yl)acrylaldehyde

50-01-1

guanidine hydrochloride

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; Reflux;71%
1144477-16-6

N-[4-(pyridin-3-yl)pyrimidin-2-yl]cyanamide

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
Stage #1: N-[4-(pyridin-3-yl)pyrimidin-2-yl]cyanamide With PYRIMIDINE; hydrazine hydrate In methanol at 50 - 60℃; for 0.25h;
Stage #2: In water
70%
420-04-2

CYANAMID

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

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

88-74-4

2-nitro-aniline

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
Stage #1: 2-nitro-aniline With nitric acid In ethanol at 0℃;
Stage #2: CYANAMID In water pH=Ca. 3; Reflux;
Stage #3: 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one In isopropyl alcohol Reflux;
70%
593-85-1

diguanidine carbonate

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

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With sodium hydroxide In butan-1-ol at 120℃; for 2h;66%
In iso-butanol for 24h; Heating / reflux;

guanidine nitrate

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

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

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
With sodium hydroxide In butan-1-ol at 120℃; for 4h; Reflux;60%
350-03-8

methyl-3-pyridylketone

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2-dimethoxy-propane / 5,5-dimethyl-1,3-cyclohexadiene / 20 h / 140 °C / Reflux
2: sodium hydroxide / butan-1-ol / 4 h / 120 °C / Reflux
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide; 5,5-dimethyl-1,3-cyclohexadiene / 16 h / Reflux
2: sodium hydroxide / butan-1-ol / 24 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: 5,5-dimethyl-1,3-cyclohexadiene / 20 h / 140 °C / Inert atmosphere; Schlenk technique
2: sodium hydroxide / butan-1-ol / 12 h / Inert atmosphere; Schlenk technique; Reflux
View Scheme
626-55-1

3-Bromopyridine

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; diethyl ether / 1 h / -78 °C / Inert atmosphere
1.2: 1.67 h / -30 - 0 °C
1.3: 0.25 h / 0 - 20 °C
2.1: ammonium hydroxide / water / 16 h / 80 °C / Sealed tube
View Scheme
104901-43-1

methyl 3-bromo-4-methylbenzoate

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

917392-54-2

methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate

Conditions
ConditionsYield
With C43H63ClNO2PPd; caesium carbonate In 1,4-dioxane at 120℃; for 1.5h; Inert atmosphere;95%
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate In 1,4-dioxane at 120℃; for 1.5h; Inert atmosphere;81%
104-88-1

4-chlorobenzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

108-59-8

malonic acid dimethyl ester

(-)-dimethyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;95%
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

5-chloro-4-(pyridin-3-yl)pyrimidin-2-amine

Conditions
ConditionsYield
With 1-chloro-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one In N,N-dimethyl-formamide at 20℃; for 12h; regioselective reaction;94%
13195-64-7

diisopropyl malonate

104-88-1

4-chlorobenzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

(-)-di-isopropyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;94%
98-01-1

furfural

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

105-53-3

diethyl malonate

(+)-diethyl 2-(furan-2-yl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)-malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;94%
104-88-1

4-chlorobenzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

105-53-3

diethyl malonate

(+)-diethyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;93%
98-01-1

furfural

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

105-53-3

diethyl malonate

(-)-diethyl 2-(furan-2-yl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)-malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;93%
100-52-7

benzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

108-59-8

malonic acid dimethyl ester

(-)-dimethyl 2-(phenyl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;93%

3-acetyl-4-methyl-2-oxo-2H-benzopyran-7-yltrifluoromethanesulfonate

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

3-acetyl-4-methyl-7-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}-2H-benzopyran-2-one

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; Buchwald-Hartwig Coupling; Inert atmosphere;93%
581076-59-7

N-(3-bromo-4-methylphenyl)-4-((4-methylpiperazin-1-yl)-methyl)benzamide

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

152459-95-5

imatinib

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 5h; Temperature;92%
Stage #1: N-(3-bromo-4-methylphenyl)-4-((4-methylpiperazin-1-yl)-methyl)benzamide; 4-pyridin-3-ylpyrimidin-2-ylamine In ethanol at 60℃; for 3h; Inert atmosphere;
Stage #2: With sodium hydroxide In water pH=8.7; Reagent/catalyst;
91%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene for 5.16667h; Inert atmosphere; Reflux; Sonication;72%
104-88-1

4-chlorobenzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

105-53-3

diethyl malonate

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

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;92%
66-25-1

hexanal

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

105-53-3

diethyl malonate

(-)-diethyl 2-(1-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)hexyl)malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;91%
100-52-7

benzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

108-59-8

malonic acid dimethyl ester

(+)-dimethyl 2-(phenyl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;91%
7745-93-9

2-bromo-4-nitrotoluene

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

152460-09-8

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

Conditions
ConditionsYield
With copper(I) iodide; sodium hydroxide In water at 60℃; for 9h;90%
With copper(l) iodide; potassium carbonate In 1,4-dioxane at 20 - 120℃; Sealed tube; Inert atmosphere;83.7%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; for 20h; Inert atmosphere; Sealed tube;83.7%
13195-64-7

diisopropyl malonate

104-88-1

4-chlorobenzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

(+)-di-isopropyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;90%
13195-64-7

diisopropyl malonate

66-25-1

hexanal

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

(-)-di-isopropyl 2-(1-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)hexyl)malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;90%
123-11-5

4-methoxy-benzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

105-53-3

diethyl malonate

(+)-diethyl ((4-methoxyphenyl)-2-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)-methyl)malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;90%
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

108-59-8

malonic acid dimethyl ester

2043-61-0

cyclohexanecarbaldehyde

(+)-dimethyl (cyclohexyl-2-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;90%
926922-18-1

3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

641571-10-0

nilotinib

Conditions
ConditionsYield
With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; tert-butyl alcohol at 100℃; for 7h;89%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane; tert-butyl alcohol at 100℃; for 7h;89%
13195-64-7

diisopropyl malonate

66-25-1

hexanal

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

(+)-di-isopropyl 2-(1-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)hexyl)malonate

Conditions
ConditionsYield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;88%
104-87-0

4-methyl-benzaldehyde

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

108-59-8

malonic acid dimethyl ester

(-)-dimethyl 2-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)(p-tolyl)methyl)-malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;88%
109-01-3

1-methyl-piperazine

1072105-05-5

N-(3-bromo-4-methylphenyl)-4-(chloromethyl)benzamide

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

152459-95-5

imatinib

Conditions
ConditionsYield
With copper(l) iodide; sodium acetate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;86%
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

108-59-8

malonic acid dimethyl ester

2043-61-0

cyclohexanecarbaldehyde

(-)-dimethyl (cyclohexyl-2-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions
ConditionsYield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;86%
106-39-8

bromochlorobenzene

66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

N-(4-chlorophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

Conditions
ConditionsYield
With copper(l) iodide; N,N'-dibenzylethanediamide; potassium tert-butylate In tert-butyl alcohol at 100℃; for 24h; Molecular sieve; Schlenk technique; Inert atmosphere;86%
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    66521-66-2

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    66521-66-24-(3-Pyridinyl)-2-aminopyrimidine

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  • 4-(pyridin-3-yl)pyrimidin-2-amine

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    4-(pyridin-3-yl)pyrimidin-2-amine

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Chemistry

Following is the structure of 2-Pyrimidinamine,4-(3-pyridinyl)- (CAS NO.66521-66-2):
                      
Empirical Formula: C9H8N4
Molecular Weight: 172.1866
Index of Refraction: 1.641
Molar Refractivity: 49.35 cm3
Molar Volume: 136.6 cm3
Density: 1.259 g/cm3
Flash Point: 250 °C
Surface Tension: 65.5 dyne/cm
Enthalpy of Vaporization: 69.7 kJ/mol
Boiling Point of 2-Pyrimidinamine,4-(3-pyridinyl)- (CAS NO.66521-66-2): 439.9 °C at 760 mmHg
Vapour Pressure of 2-Pyrimidinamine,4-(3-pyridinyl)- (CAS NO.66521-66-2): 6.13E-08 mmHg at 25 °C
SMILES: Nc1nc(ccn1)c2cnccc2
InChI: InChI=1/C9H8N4/c10-9-12-5-3-8(13-9)7-2-1-4-11-6-7/h1-6H,(H2,10,12,13)
InChIKey: LQHQKYWYKPLKCH-UHFFFAOYAE

Specification

 2-Pyrimidinamine,4-(3-pyridinyl)- , its cas register number 66521-66-2. It also can be called 4-(Pyridin-3-yl)pyrimidin-2-amine ; and 4-pyridin-3-ylpyrimidin-2-amine .