Hydrogen Bromide → 2-benzylpyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-benzyl-4-methoxypyrimidine (0.675 g, 3.37 mmol) in AcOH (15 mL) was added HBr (2.28 mL, 20.2 mmol; 48 wt % in H2O). The reaction mixture was stirred at 95° C. for 2 hours. The reaction mixture was cooled to room temperature and diluted with H2O. The pH of the reaction mixture was adjusted to 5-6 with 6 M aqueous NaOH and then partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude yellow solid. Purification of the crude product was achieved by trituration with dichloromethane and diethyl ether. The resulting solid was filtered, washed with diethyl ether, collected and dried under vacuum to yield the desired product (0.531 g, 85%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.79 (d, J=6.6 Hz, 1H), 7.31 (m, 4H), 7.23 (m, 1H), 6.10 (d, J=6.6 Hz, 1H), 3.83 (s, 2H). LRMS (ESI pos) m/e 187 (M+1).

Provenance & Evidence