74-69-1

Basic information

• Product Name: 4-Pyrimidinamine, 2-methyl- (9CI)
• Synonyms: 4-Pyrimidinamine, 2-methyl- (9CI);2-methylpyrimidin-4-amine;4-Amino-2-methylpyrimidine;2-Methyl-4-pyrimidinamine;4-PyriMidinaMine,2-Methyl;2-Methyl-4-Pyrimidinamine(WX606010);PKR-00635
• CAS NO: 74-69-1
• Molecular Formula: C₅H₇N₃
• Molecular Weight: 109.12918
• EINECS: 205-525-8
• Product Categories: PYRIMIDINE
• Mol File: 74-69-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 204-205℃
• Boiling Point: 222℃
• Flash Point: 111℃
• Appearance: /
• Density: 1.155
• Vapor Pressure: 0.103mmHg at 25°C
• Refractive Index: 1.582
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.99±0.10(Predicted)
• CAS DataBase Reference: 4-Pyrimidinamine, 2-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pyrimidinamine, 2-methyl- (9CI)(74-69-1)
• EPA Substance Registry System: 4-Pyrimidinamine, 2-methyl- (9CI)(74-69-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 74-69-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 7, p. 4325, 1966 DOI: 10.1016/0005-2760(66)90119-6

InChI:InChI=1/C5H7N3/c1-4-7-3-2-5(6)8-4/h2-3H,1H3,(H2,6,7,8)

Upstream product

• 5053-43-0 2-methylpyrimidine 
• 4994-86-9 4-chloro-2-methylpyrimidine 
• 7664-41-7 ammonia 

Downstream Products

• 855230-90-9 4-nitro-benzenesulfonic acid-(2-methyl-pyrimidin-4-ylamide) 
• 1334407-44-1 2-(2,6-dichlorophenyl)-N-(2-methylpyrimidin-4-yl)-3H-imidazo-[4,5-c]pyridin-4-amine 
• 1620998-23-3 N-(2-methylpyrimidin-4-yl)-5-trifluoromethylphthalamic acid tert-butyl ester 
• 1620997-28-5 2-((2-methylpyrimidin-4-yl)carbamoyl)-4,5-bis(trifluoromethyl)benzoic acid 
• 1453853-24-1 (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-((2-methylpyrimidin-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one 
• 1448541-18-1 N-(2-methylpyrimidin-4-yl)-2-[3-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]acetamide 
• 1196091-83-4 (R)-1-[(2-Methyl-pyrimidin-4-ylcarbamoyl)-methyl]-3-(1-phenyl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane chloride 
• 1187324-70-4 1-(3,4-dimethylphenyl)-5-methyl-N-(2-methyl-4-pyrimidinyl)-1H-1,2,3-triazole-4-carboxamide 
• 1187324-68-0 1-(3-chloro-4-fluorophenyl)-5-methyl-N-(2-methyl-4-pyrimidinyl)-1H-1,2,3-triazole-4-carboxamide 
• 1068569-82-3 C₁₇H₁₃N₅S 
• 588941-11-1 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(2-methyl-pyrimidin-4-yl)-propionamide 
• 588941-78-0 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(2-methyl-pyrimidin-4-yl)-propionamide 
• 588942-68-1 3-cyclopentyl-2-(4-methanesulfonyl-3-nitro-phenyl)-N-(2-methyl-pyrimidin-4-yl)-propionamide 
• 599-84-8 sulphamerazine 

Relevant articles and documents

On the Chichibabin Amination of Pyrimidine and N-Alkylpyrimidinium Salts Using Liquid Ammonia/Potassium Permanganate

Treatment of the 2-R-pyrimidines (1, R = methyl, ethyl, i-propyl and t-butyl) with potassium amide/liquid ammonia/potassium permanganate leads to amination at C-4(6).The yields of the 4(6)-amino compounds 3 increase in the order 2-methyl (10percent), 2-ethyl (30percent), 2-i-propyl (45percent) and 2-t-butyl (60percent).Treatment of the 2-R-N-methylpyrimidinium salts (4, R = hydrogen, methyl) with liquid ammonia/potassium permanganate leads to a regiospecific imination at C-6, the corresponding 2-R-1,6-dihydro-6-imino-1-methylpyrimidines 6 being obtained in 80-85percent yield.It is proved by 15N-labelling that no ring opening is involved in these imination reactions.Treatment of the imino compounds with base leads to the corresponding 2-R-6-methylaminopyrimidines 8, involving, as proved by 15N-labelling, an ANRORC-mechanism. 2-t-Butyl-1-ethylpyrimidinium tetrafluoroborate (9b) when treated with liquid ammonia/potassium permanganate undergoes N-deethylation, 2-t-butylpyrimidine being exclusively formed.