Sodium Carbonate → 3-(4-chlorobenzyl)-5-(4-(benzyloxy)-3-fluorophenyl)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask was added 3-(4-chlorobenzyl)-5-bromopyrimidin-4(3H)-one (0.388 g, 1.30 mmol), 4-benzyloxy-3-fluorophenylboronic acid (0.382 g, 1.55 mmol), Pd(PPh3)4 (0.0748 g, 0.0648 mmol), LiCl (0.275 g, 6.48 mmol), dioxane (10 mL) and 2 M aqueous sodium carbonate solution (5 mL). The reaction mixture was stirred at 10° C. for 1 hour, then quenched the reaction by pouring the mixture into water 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 (0.17 g, 31.2% yield). LRMS (APCI pos) m/e 421.0 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.15 (s, 1H), 8.02 (s, 1H), 7.49-7.54 (m, 1H), 7.42-7.46 (m, 2H), 7.36-7.41 (m, 3H), 7.32-7.35 (m, 5H), 5.18 (s, 2H), 5.12 (s, 2H).

Provenance & Evidence