N,N-Dimethylaniline → Methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

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Reaction Conditions

Reaction Steps

A mixture of methyl [4-hydroxy-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (4.0 g, 13.19 mmol), phosphorus oxychloride (6.15 mL, 65.95 mmol) and N,N-dimethylaniline (2.51 mL, 19.78 mmol) was stirred at 150° C. for 3 hours. After the removal of the excess phosphorus oxychloride, the residue was dissolved with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica-gel, (hexane:ethyl acetate, 7/3) to give methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (2.70 g, 64%) as orange solid.

Provenance & Evidence