Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate → (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (LiAlH4) (1.140 g, 30 mmol) in THF (100 mL) was added ethyl 4-(methylamino)-2-(methylthio)pyrimidine-5-carboxylate (4.536 g, 20 mmol), and the reaction mixture was stirred at room temperature for 2 hours. The solution was carefully quenched with H2O (2 mL), sodium hydroxide (NaOH) (aq., 15%, 2 mL) and additional H2O (7 mL), and then stirred for 1 hour. The mixture was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to give (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (3.2 g, 85%) as a yellowish solid. MS (ES+) C7H11N3OS requires: 185. found: 186 [M+H]+.

Provenance & Evidence