Ammonium Chloride → HCID 68227170, compound

Participants

Reaction Steps

(Methoxymethyl)triphenylphosphonium chloride (68.6 g, 0.2 mol) was dissolved in THF (1000 mL), and lithium diisopropylamide (100 mL, 0.2 mol) was added to the solution at −20° C. After stirring at room temperature for 0.5 hour, the solution of 2-(methylthio)pyrimidine-4-carbaldehyde (15.4 g, 0.1 mol) in THF (400 mL) was added to the solution dropwise. The reaction mixture was stirred at room temperature overnight. Then saturated aqueous ammonium chloride solution (200 mL) was added to the mixture, extracted with ethyl acetate (1500 mL), and dried over with anhydrous sodium sulfate. The organic layer was concentrated and purified by chromatography (petroleum ether:ethyl acetate, 3:1) to give 4-(2-methoxy-vinyl)-2-methylsulfanyl-pyrimidine as a yellow solid. (Yield 11.2 g, 61.2%). LC-MS: [M+H]+ 183.

Provenance & Evidence