Methyl chloroacetate → (2-Amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester

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Reaction Steps

Following the method of Perez et al. (Synthesis 1983, 402), to a stirred solution of 1.0 g (4.4 mmol) 2-amino-4-phenyl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile in 50 ml methanol were added 1.0 ml (5.4 mmol) sodium methylate solution (5.4M in methanol) and 0.39 ml (4.4 mmol) methyl chloroacetate and stirring continued for 3 hours at reflux. The reaction mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried over sodium sulfate and concentrated in vacuo. Chromatography (1/1 ethyl acetate/hexane) followed by trituration in 8/1 ethyl acetate/methanol afforded 0.41 g (32%) (2-Amino-5-cyano-6-phenyl-pyrimidin-4-ylsulfanyl)-acetic acid methyl ester as a light yellow crystalline solid. EI-MS m/e (%): 300 (M+, 38), 299 ([M—H]+, 100), 241 (74), 240 (50).

Provenance & Evidence