Sodium hydride → 2-Methylpyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate

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Reaction Steps

To an ice-cooled mixture of 2-methyl-5hydroxypyrimidine (0.9 g) and sodium hydride 80% (0.24 g) in dimethylacetamide (15 ml), a solution of 1-cyclohexylcyclohexane-1-carbonyl chloride (1.68 g) in dimethylacetamide (10 ml) was added. The mixture was then stirred at room temperature for 1 hour, then filtered and evaporated in vacuo. The residue was taken up with ethyl acetate, which was washed with water and dried. Evaporation of the solvent and column chromatography (cyclohexane/ethyl acetate 9:1) afforded 1.2 g of 2-methylpyrimidin-5-yl 1-cyclohexylcyclohexane-1-carboxylate. M.p. 52°-55° C. According to the procedure above described the following compound was also prepared, 2-methylpyrimidin-5-yl α-cyclopentylphenyl glicolate hydrochloride. M.p. 132°-138° C.

Provenance & Evidence