4-Methoxybenzyl alcohol → HCID 86756060, compound

Participants

Reaction Steps

An ice-cooled suspension of 2.1 g (53 mmol) of sodium hydride (60% w/w dispersion in mineral oil) in 120 ml of tetrahydrofuran was treated dropwise with a solution of 6.5 g (47 mmol) of 4-methoxybenzyl alcohol in 40 ml of tetrahydrofuran. After 30 minutes, a solution of 10 g (43 mmol) of ethyl 4-chloro-2-methylthiopyrimidine-5-carboxylate was added slowly. After a further 40 minutes the reaction was quenched by the cautious addition of 60 ml of saturated aqueous ammonium chloride. The mixture was separated and the organic phase dried over magnesium sulfate, filtered and evaporated to give 14.2 g (99%) of ethyl 4-(4-methoxy-benzyloxy)-2-methylthiopyrimidine-5-carboxylate as a pale yellow oil. [Mass spectrum (ESI) MH+ =335].

Provenance & Evidence