942189-65-3

A mixture of tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.259 mmol) and cesium carbonate (1.15 g, 3.03 mmol) was added to a mixture of 2-bromopyrimidine (0.43 g, 2.70 mmol) and 2-bromopyridine-5-boronic acid (0.55 g, 2.72 mmol) and reacted overnight at a reflux temperature in a MeOH/toluene/water (15 mL, v/v/v/a 1:1 :1) in a solvent mixture of MeOH/toluene/water (15 mL, v/v ratio 1:1), and the reaction was stirred at reflux temperature overnight. After completion of the reaction, the mixture was cooled to room temperature and diluted with EtOAc (200 mL) and water (50 mL). The organic layer was separated, dried with anhydrous MgSO4, filtered and the solvent was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with 25% v/v EtOAc/hexane as eluent to afford the target compound 2-(6-bromopyridin-3-yl)pyrimidine (76) as a white solid (0.55 g, 85% yield).ESMS (MH+): m/z 236.

[1] Patent: WO2007/70398, 2007, A1. Location in patent: Page/Page column 226
[2] Patent: WO2008/156739, 2008, A1. Location in patent: Page/Page column 210-211
[3] Patent: WO2007/97937, 2007, A1. Location in patent: Page/Page column 183