Electric Literature of 31058-83-0 , The common heterocyclic compound, 31058-83-0, name is 6-Chloro-N,N-dimethylpyrimidin-4-amine, molecular formula is C6H8ClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
A mixture ofN-(cis-4-bromo-2-trifluoromethoxy-benzyl)-cyclohexane-1, 4- diamine (466 mg), (6-chloro-pyrimidin-4-yl) -dimethyl-amine (200 mg), and ethylene glycol (0.5 mL) was stirred at reflux for 4 hr in a sealed tube. The mixture was poured into saturated aqueous NaHC03 and the aqueous layer was extracted with CHC13 (three times). The combined organic layer was dried over MgS04, filtered, concentrated under reduced pressure, and purified by flash chromatography (NH-silica gel, 50% EtOAc in hexane and silica gel, 501-‘o MeOH in CHCl3) to give N’- (cis-4- { [4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N, N-dimethylpyrimidine-4, 6-diamine. To a solution of the above material in EtOAc (2 mL) was added 4 M hydrogen chloride in EtOAc (10 mL). The mixture was stirred at ambient temperature for 1 hr and concentrated under reduced pressure. The residue was suspended in Et2O (20 mL) and the suspension was stirred at ambient temperature for 4 hr. The precipitate was collected by filtration, washed with Et2O, and dried under reduced pressure to give N’-(cis-4-{[4-bromo-2- (trifluoromethoxy) benzyl] amino} cyclohexyl)-N,N-dimethylpyrimidine-4, 6-diamine dihydrochloride (67 mg). ESI MS m/e 488, M (free) + H+ ;’H NMR (300 MHz, CDC13) 8 1.64-1. 86 (m, 2 H), 1.96- 2.34 (m, 8 H), 2. 98-3.44 (m, 8 H), 4.27 (s, 2 H), 7.40-7. 59 (m, 3 H), 8.06-8. 24 (m, 2 H).
The synthetic route of 31058-83-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; Arena Pharmaceuticals, Inc; WO2005/95357; (2005); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia