66521-66-2

Basic information

• Product Name: 4-(3-Pyridinyl)-2-aminopyrimidine
• Synonyms: BUTTPARK 41\09-83;4-(3-PYRIDINYL)-2-PYRIMIDINAMINE;4-(3-PYRIDINYL)-2-PYRIMIDINE AMINE;4-(3-PYRIDINYL)-2-PYRIMIDINYLAMINE;4-(PYRIDIN-3-YL)PYRIMIDIN-2-AMINE;4-(3-Pyridyl)-2-pyrimidinamine;4-(3-Pyridinyl)-2-aminopyrimidine;4-(3-Pyridyl)-2-pyrimidineamine
• CAS NO: 66521-66-2
• Molecular Formula: C₉H₈N₄
• Molecular Weight: 172.19
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 66521-66-2.mol
• Article Data: 35

Chemical Properties

• Melting Point: 189-191 °C
• Boiling Point: 439.9 °C at 760 mmHg
• Flash Point: 250 °C
• Appearance: /
• Density: 1.259 g/cm³
• Vapor Pressure: 6.13E-08mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.76±0.10(Predicted)
• CAS DataBase Reference: 4-(3-Pyridinyl)-2-aminopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-Pyridinyl)-2-aminopyrimidine(66521-66-2)
• EPA Substance Registry System: 4-(3-Pyridinyl)-2-aminopyrimidine(66521-66-2)

Safety Data

• Hazard Codes: T
• Statements: 25-20/21/22
• Safety Statements: 45-36/37
• Hazardous Substances Data: 66521-66-2(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

Uses

Intermediate in the preparation of Nilotinib.

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)

Synthetic route

guanidine nitrate (506-93-4) + (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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

guanidine hydrochloride (50-01-1) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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%

2-chloro-4-(pyridin-3-yl)pyrimidine (483324-01-2) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
With ammonium hydroxide In water at 80℃; for 16h; Sealed tube;	87%

guanidine nitrate (506-93-4) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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

2-amino-4-chloropyrimidine (3993-78-0) + 3-pyridylboronic acid (1692-25-7) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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%

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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

guanidine hydrochloride (50-01-1) + (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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

(Z)-3-chloro-3-(pyridin-3-yl)acrylaldehyde (1392279-39-8) + guanidine hydrochloride (50-01-1) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
With potassium carbonate In methanol at 20℃; Reflux;	71%

N-[4-(pyridin-3-yl)pyrimidin-2-yl]cyanamide (1144477-16-6) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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%

CYANAMID (420-04-2) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) + 2-nitro-aniline (88-74-4) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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%

diguanidine carbonate (593-85-1) + 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

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

guanidine nitrate + (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one (55314-16-4, 75415-01-9, 123367-26-0) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
With sodium hydroxide In butan-1-ol at 120℃; for 4h; Reflux;	60%

methyl-3-pyridylketone (350-03-8) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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

3-Bromopyridine (626-55-1) → 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2)

Conditions	Yield
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

methyl 3-bromo-4-methylbenzoate (104901-43-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate (917392-54-2)

Conditions	Yield
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%

4-chlorobenzaldehyde (104-88-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + malonic acid dimethyl ester (108-59-8) → (-)-dimethyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	95%

4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → 5-chloro-4-(pyridin-3-yl)pyrimidin-2-amine

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

diisopropyl malonate (13195-64-7) + 4-chlorobenzaldehyde (104-88-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → (-)-di-isopropyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	94%

furfural (98-01-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + diethyl malonate (105-53-3) → (+)-diethyl 2-(furan-2-yl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)-malonate

Conditions	Yield
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%

4-chlorobenzaldehyde (104-88-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + diethyl malonate (105-53-3) → (+)-diethyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
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%

furfural (98-01-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + diethyl malonate (105-53-3) → (-)-diethyl 2-(furan-2-yl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)-malonate

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

benzaldehyde (100-52-7) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + malonic acid dimethyl ester (108-59-8) → (-)-dimethyl 2-(phenyl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

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

3-acetyl-4-methyl-2-oxo-2H-benzopyran-7-yltrifluoromethanesulfonate + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → 3-acetyl-4-methyl-7-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}-2H-benzopyran-2-one

Conditions	Yield
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%

N-(3-bromo-4-methylphenyl)-4-((4-methylpiperazin-1-yl)-methyl)benzamide (581076-59-7) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → imatinib (152459-95-5)

Conditions	Yield
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%

4-chlorobenzaldehyde (104-88-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + diethyl malonate (105-53-3) → (-)-diethyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	92%

hexanal (66-25-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + diethyl malonate (105-53-3) → (-)-diethyl 2-(1-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)hexyl)malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	91%

benzaldehyde (100-52-7) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + malonic acid dimethyl ester (108-59-8) → (+)-dimethyl 2-(phenyl((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
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%

2-bromo-4-nitrotoluene (7745-93-9) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → N-(5-nitro-2-methylphenyl)-4-(3-pyridinyl)-2-pyrimidineamine (152460-09-8)

Conditions	Yield
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%

diisopropyl malonate (13195-64-7) + 4-chlorobenzaldehyde (104-88-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → (+)-di-isopropyl 2-((4-chlorophenyl)((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
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%

diisopropyl malonate (13195-64-7) + hexanal (66-25-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → (-)-di-isopropyl 2-(1-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)hexyl)malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	90%

4-methoxy-benzaldehyde (123-11-5) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + diethyl malonate (105-53-3) → (+)-diethyl ((4-methoxyphenyl)-2-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)-methyl)malonate

Conditions	Yield
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%

4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + malonic acid dimethyl ester (108-59-8) + cyclohexanecarbaldehyde (2043-61-0) → (+)-dimethyl (cyclohexyl-2-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
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%

3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (926922-18-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → nilotinib (641571-10-0)

Conditions	Yield
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%

diisopropyl malonate (13195-64-7) + hexanal (66-25-1) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → (+)-di-isopropyl 2-(1-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)hexyl)malonate

Conditions	Yield
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%

4-methyl-benzaldehyde (104-87-0) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + malonic acid dimethyl ester (108-59-8) → (-)-dimethyl 2-(((4-(pyridin-3-yl)pyrimidin-2-yl)amino)(p-tolyl)methyl)-malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	88%

1-methyl-piperazine (109-01-3) + N-(3-bromo-4-methylphenyl)-4-(chloromethyl)benzamide (1072105-05-5) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → imatinib (152459-95-5)

Conditions	Yield
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%

4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) + malonic acid dimethyl ester (108-59-8) + cyclohexanecarbaldehyde (2043-61-0) → (-)-dimethyl (cyclohexyl-2-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)methyl)malonate

Conditions	Yield
With quinine In neat liquid at 50℃; for 48h; Mannich Aminomethylation; enantioselective reaction;	86%

bromochlorobenzene (106-39-8) + 4-pyridin-3-ylpyrimidin-2-ylamine (66521-66-2) → N-(4-chlorophenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

Conditions	Yield
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%

Upstream product

• 483324-01-2 2-chloro-4-(pyridin-3-yl)pyrimidine 
• 626-55-1 3-Bromopyridine 
• 1392279-39-8 (Z)-3-chloro-3-(pyridin-3-yl)acrylaldehyde 
• 50-01-1 guanidine hydrochloride 
• 3993-78-0 2-amino-4-chloropyrimidine 
• 1692-25-7 3-pyridylboronic acid 
• 55314-16-4 (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 350-03-8 methyl-3-pyridylketone 
• 420-04-2 CYANAMID 
• 55314-16-4 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 88-74-4 2-nitro-aniline 
• 1144477-16-6 N-[4-(pyridin-3-yl)pyrimidin-2-yl]cyanamide 
• 506-93-4 guanidine nitrate 
• 593-85-1 diguanidine carbonate 

Downstream Products

• 641571-10-0 nilotinib 
• 112675-67-9 N-(4-methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine 
• 1048003-91-3 N-(2,4-dimethylbenzyl)-4-(pyridin-3-yl)pyrimidin-2-amine 
• 917392-54-2 methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate 
• 152459-95-5 imatinib 
• 1346617-84-2 N-(5-azido-2-methylphenyl)-4-(pyridine-3-yl)pyrimidin-2-amine 
• 1346617-86-4 N-[2-methyl-5-(4-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}-1H-1,2,3-triazol-1-yl)phenyl]-4-(pyridine-3-yl)pyrimidin-2-amine 
• 152460-10-1 6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine 
• 895519-84-3 4-((4-ethylpiperazin-1-yl)methyl)-N-(6-methyl-5-(4-(pyridin-3-yl)pyrimidin-2-ylamino)pyridin-3-yl)benzamide 
• 404844-11-7 4-(chloromethyl)-N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]-amino}phenyl)benzamide 
• 796738-20-0 4-((4-methyl-1,4-diazepan-1-yl)methyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide 
• 1427026-59-2 C₃₀H₃₅N₇O 
• 404843-98-7 N-(4-methyl-3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)phenyl)-4-(morpholinomethyl)benzamide 
• 796738-54-0 4-(4-methylpiperazin-1-ylmethyl)-N-[4-fluoro-3-(4-(pyridin-3-yl)pyrimidin-2-yl)aminophenyl]benzamide 

Relevant articles and documents

Navigating into the chemical space between MGCD0103 and SAHA: Novel histone deacetylase inhibitors as a promising lead

Histone deacetylase inhibitors (HDIs) are an increasingly important class of cancer-targeting agents. Two kinds of small molecule histone deacetylase inhibitors, mainly employing the motifs of the two known HDAC inhibitors MGCD0103 and SAHA as the basic scaffolds, were designed, synthesized and evaluated for the preliminary biological activity. Strikingly, these two compounds regained a long half-life potency like MGCD0103 and retained the non-selectivity for HDAC1 versus HDAC6 derived from SAHA. Together, these two compounds combining both the advantages of MGCD0103 and SAHA could be considered as novel histone deacetylase inhibitors in targeted drug development and possibly anticipated to be more effective under the clinical trials.

Synthesis of imatinib, a tyrosine kinase inhibitor, labeled with carbon-14

Imatinib (Gleevec) is a multiple tyrosine kinase inhibitor that decreases the activity of the fusion oncogene called BCR-ABL (breakpoint cluster region protein-Abelson murine leukemia viral oncogene homolog) and is clinically used for the treatment of chronic myelogenous leukemia and acute lymphocytic leukemia. Small molecule drugs, such as imatinib, can bind to several cellular proteins including the target proteins in the cells, inducing undesirable effects along with the effects against the disease. In this study, we report the synthetic optimization for 14C-labeling and radiosynthesis of [14C]imatinib to analyze binding with cellular proteins using accelerator mass spectroscopy. 14C-labeling of imatinib was performed by the synthesis of 14C-labeld 2-aminopyrimidine intermediate using [14C]guanidine·HCl, which includes an in situ reduction of an inseparable byproduct for easy purification by HPLC, followed by a cross-coupling reaction with aryl bromide precursor. The radiosynthesis of [14C]imatinib (specific activity, 631 MBq/mmol; radiochemical purity, 99.6%) was achieved in six steps with a total chemical yield of 29.2%.

Smo inhibitor as well as synthesis method and application thereof

The invention discloses an Smo inhibitor as well as a synthesis method and application thereof. A structural formula of the Smo inhibitor is shown by a formula (I) as shown in the specification. The invention also discloses the synthesis method and the application of the Smo inhibitor. According to the invention, nilotinib is optimized into the dual-targeted inhibitor being active against Smo andBcr-Abl, and the inhibitor can overcome the tolerance problem caused by single-targeted drugs, has the advantages of improving anti-tumor efficacy and reducing toxic or side effects, and provides a reference for future research on dual-targeted anti-hematologic malignant drugs.