Methyl 2-(Methylthio)pyrimidine-5-carboxylate → (2-(Methylsulfanyl)pyrimidin-5-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(methylsulfanyl)pyrimidine-5-carboxylate (N1) (023 g, 1.2 mmol) in 20 mL THF at −78° C. was added diisobutylaluminum hydride (3.2 mL, 1.0 M solution in toluene). The reaction mixture stirred for 40 min at −78° C., and then additional diisobutylaluminum hydride (5 eq.) was added dropwise. The reaction mixture was stirred for 2 h, and then quenched with concentrated acetic acid. The reaction mixture was warmed to room temperature and filtered to obtain a biphasic solution. The layers were separated, and the organics were dried over sodium sulfate, filtered, and concentrated to afford [2-(methylsulfanyl)pyrimidin-5-yl]methanol (N2) that gave a mass ion (ES+) of 157.1 for M+H+.

Provenance & Evidence