Methanol → 5-bromo-2-(phenylamino)pyrimidin-4(3H)-one

Participants

Reaction Steps

To a suspension of 2-(phenylamino)pyrimidin-4(3H)-one (0.200 g, 1.07 mmol) in CHCl3 (5 mL) and a small amount of MeOH at 0° C. was added bromine (0.0547 ml, 1.07 mmol). The reaction was stirred for 40 minutes, diluted with H2O, and then quenched with 10% sodium bisulfite solution. The reaction mixture was diluted with EtOAc, the layers were separated and the aqueous layer was re-extracted with EtOAc (1×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The product was obtained (0.284 g; 100%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ 11.32 (br s, 1H), 8.89 (br s, 1H), 8.04 (s, 1H), 7.55 (d, 2H), 7.33 (m, 2H), 7.06 (t, 1H). LRMS (ESI pos) m/e 266, 268 (M+, Br pattern).

Provenance & Evidence