Sodium Hydroxide → 4-Methoxy-2-(methylsulfanyl)pyrimidine-5-carboxylic acid

Participants

Reaction Steps

To a solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (24.40 g, 104.9 mmol) in MeOH (125 mL) was added solid sodium methoxide (11.40 g, 211.0 mmol) at rt. The reaction mixture was stirred at rt for 5 h and then treated with NaOH (17.70 g, 315.5 mmol) in H2O (100 mL). It was then stirred at the same temperature for an additional 1 h. The reaction mixture was concentrated to half of the volume and then acidified to pH=4 with HCl (6N). The reaction was extracted with EtOAc (5×200 mL) and the organic layer was washed with brine (200 mL), dried over Na2SO4, and concentrated to yield the desired product as a white solid (19.28 g, 92%). MS (m/z): 201 (MH+). 1H NMR (DMSO-d6) δ: 8.72 (s, 1H), 3.98 (s, 3H), 2.54 (s, 3H).

Provenance & Evidence