Electric Literature of 76537-18-3,Some common heterocyclic compound, 76537-18-3, name is 3-Bromo-5-chloropyrazin-2-amine, molecular formula is C4H3BrClN3, 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.
To a degassed solution of 3-bromo-5-chloro-pyrazin-2-amine, la, (20.80 g, 99.79 mmol), Et3N (41.74 mL, 299.4 mmol), iodocopper (0.6 g, 2.99 mmol) and dichloropalladium; triphenylphosphine (1.40 g, 2.00 mmol) in THF (388 mL) was added ethynyl-trimethyl-silane (14.10 mL, 99.79 mmol) over 5 minutes. The reaction mixture was warmed to 55 C for 1 hour. The reaction mixture was cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated in vacuo and the resulting solid was washed with ether and filtered to provide 14 g of the desired product (62% yield) in sufficient purity for use in the subsequent reaction: XH NMR (400 MHz, CDC13) delta 7.94 (s, 1H), 5.00 (d, J = 44.2 Hz, 2H), 0.26 (s, 9H) ppm; LCMS Gradient 10-90%, 0.1% formic acid, 5 min, C18/ACN, RT = 3.42 min (M+H) 226.39.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-5-chloropyrazin-2-amine, its application will become more common.
Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHARIFSON, Paul, S.; LEDEBOER, Mark, W.; CLARK, Michael, P.; BOYD, Michael, J.; GAO, Huai; LEDFORD, Brian; MALTAIS, Francois; PEROLA, Emanuele; WO2013/184985; (2013); A1;,
Pyrazine – Wikipedia,
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