Ethanol → (E)-4-[(4-Amino-6-chloro-2-pyrimidinyl)thio]-2-butenoic acid methyl ester

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Reaction Steps

4-Amino-6-chloro-2-mercaptopyrimidine mesylate (0.30 g, 1.16 mmol) is dissolved in 3.25N sodium hydroxide (2 ml) and ethanol (1 ml) at ambient temperature followed by the addition of methyl 4-bromocrotonate (0.16 ml, 1.40 mmol). The reaction is stirred for 2 to 15 hours, quenched with excess water, extracted with methylene chloride (2×25 ml). The extracts are combined, washed with saline (25 ml), dried over sodium sulfate, concentrated in vacuo and recrystallized from hexane/ethyl acetate to give Cpd #193. mp 146-149° C.

Provenance & Evidence