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

Participants

Reaction Steps

To a solution of 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylic acid ethyl ester (30 g, 132 mmol) in THF (300 mL) was added LiAlH4 powder (7.5 g, 198 mmol) at RT. After 1 h, the reaction was carefully quenched with H2O (10 mL) and 10% NaOH (7 mL). The mixture was stirred for 1 h and then filtered. The filtrate was concentrated to give crude (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (22.0 g, 90% yield), which was used in the next reaction without further purification. 1H NMR (300 MHz, DMSO-d6): δ 7.79 (s, 1H), 6.79 (m, 1H), 5.04 (t, J=5.4 Hz, 1H), 4.27 (d, J=5.4 Hz, 2H), 2.83 (d, J=4.8 Hz, 3H), 2.40 (s, 3H).

Provenance & Evidence