Hydrogen Bromide → 5-(2,5-difluoro-4-hydroxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

5-(2,5-difluoro-4-methoxyphenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.066 g, 0.192 mmol) was dissolved in AcOH (2 mL) and HBr (1.087 ml, 9.612 mmol; 48 wt % in H2O) was added. The mixture was stirred at 125° C. for 3 days. The reaction mixture was cooled to room temperature and then diluted with H2O. The pH of the reaction mixture was adjusted to a pH of about 5 with 6M aqueous NaOH, which resulted in the formation of an off-white precipitate that was filtered and washed with H2O. The solid was dried directly in the fritted funnel under vacuum overnight and then dissolved through with MeOH/THF and concentrated. The product was obtained (58 mg; 92%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 10.33 (br s, 1H), 8.91 (br s, 1H), 7.70 (s, 1H), 7.55-7.48 (m, 2H), 7.36 (t, 2H), 7.23 (m, 1H), 7.14 (m, 1H), 6.77 (m, 1H), 3.53 (s, 3H). LRMS (ESI pos) m/e 330 (M+1).

Provenance & Evidence