Sodium hydride → 3-(4-chlorobenzyl)-5-bromopyrimidin-4(3H)-one

Participants

Reaction Steps

Sodium hydride (0.343 g, 8.57 mmol) was added to a solution of 5-bromopyrimidin-4(3H)-one (1.5 g, 8.57 mmol) in THF (10 mL) and DMF (6 mL) and the reaction mixture was stirred for 10 minutes. 4-Chlorobenzyl bromide (1.76 g, 8.57 mmol) was added and the reaction mixture was stirred for an additional 1 hour. The reaction was quenched by pouring the reaction mixture into ice and diluting with ethyl acetate. The organic layer washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (Biotage 40S) to afford the title compound as white solid (0.388 g, 15.1%). LRMS (APCI pos) m/e 300.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.20 (s, 1H), 8.10 (s, 1H), 7.29-7.37 (m, 4H), 5.15 (s, 2H).

Provenance & Evidence