2-Pyrimidinamine, 5-methyl- (9CI) Chemical Properties

Melting point:

192-193℃

Boiling point:

194.6°C (rough estimate)

Density 

1.155

refractive index 

1.5340 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

solid

pka

4.20±0.10(Predicted)

Appearance

White to yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HS Code 

2933599590

2-Pyrimidinamine, 5-methyl- (9CI) Usage And Synthesis

Uses

5-Methylpyrimidin-2-amine is a useful research chemical compound used in the preparation of highly potent macrocyclic ALK inhibitors as potential antitumors.

Synthesis

Step 1: 2-Chloro-5-methylpyrimidine (10.0 g, 77.79 mmol) was dissolved in industrial methanol (IMS, 100 mL) followed by addition of 35% ammonia (100 mL). The reaction mixture was transferred to an autoclave, sealed and reacted at 200 °C for 4 hours. Upon completion of the reaction, it was cooled to room temperature and most of the solvent was removed by concentration via rotary evaporator. Water (25 mL) was added to the residue and a solid was precipitated. The solid was collected by filtration and dried under vacuum to afford 2-amino-5-methylpyrimidine (7.85 g, 92% yield) as an off-white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 8.06 (s, 2H), 6.30 (s, 2H), 2.03 (s, 3H).LCMS analysis showed m/z 110 [M + H]+.

Purification Methods

Crystallise it from water or *benzene/pet ether and sublime it at 50o/0.5mm. [Beilstein 24 H 87.]

References

[1] Patent: WO2013/132376, 2013, A1. Location in patent: Page/Page column 205
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4720 - 4744
[3] Chemische Berichte, 1905, vol. 38, p. 3397
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 5, p. 1261 - 1266

2-Pyrimidinamine, 5-methyl- (9CI)(50840-23-8)Related Product Information

• Pirimicarb
• ETHYL 2-AMINO-4-PROPYLPYRIMIDINE-5-CARBOXYLATE
• Diaveridine
• Trimethoprim
• Pipemidic acid
• 2-AMINO-5,6-DIMETHYL-4-HYDROXYPYRIMIDINE
• 5-ACETYL-2-AMINO-4-METHYLPYRIMIDINE
• 5-(4,5-dimethoxy-2-methylbenzyl)-2,4-diaminopyrimidine
• 2-AMINO-5-CARBOETHOXY-4-HYDROXYPYRIMIDINE
• 2-AMINO-4,6-DIHYDROXY-5-METHYLPYRIMIDINE
• PIROMIDIC ACID
• ETHYL 2-AMINO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• Pyrimethamine
• BUPIRIMATE
• ETHYL 2-AMINO-4-METHYLPYRIMIDINE-5-CARBOXYLATE
• ETHIRIMOL
• 5-(4-CHLOROBENZYLOXYCARBONYL)-4-(TRIFLUOROMETHYL)PYRIMIDIN-2-YL HYDRAZINE
• 2-AMINO-6-HYDROXY-5-(B-HYDROXYETHYL)-4-METHYLPYRIMIDINE