Iodoethane → 2-Chloro-5-(ethoxymethyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of the (2-chloropyrimidin-5-yl)methanol (1 g, 6.92 mmol) in anhydrous DMF (6.92 ml) was cooled at ice-bath temperature and iodoethane (2.236 ml, 27.7 mmol) added. The solution was stirred for 10 minutes at 0° C. Sodium hydride (0.304 g, 7.61 mmol) was added and the resulting mixture stirred at 0° C. for 0.5 hours and RT for 60 minutes. The mixture was diluted with saturated ammonium chloride (100 mL) and extracted with EtOAc (3×50 mL). The organic fractions were combined, washed with brine (100 mL), dried over Na2SO4, filtered and the volatiles removed in vac. The mixture was purified on a 50 g Biotage KP-SiO2 cartridge using a gradient eluant of 0-100% EtOAc:Hexanes, to afford the title compound. LC/MS (m/z): 173 (M+H)+.

Provenance & Evidence