m-Toluidine → Methyl 2-chloro-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

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Reaction Steps

A mixture of methyl 2,4-dichloro-6-methylpyrimidine-5-carboxylate (940 mg, 4.25 mmol), m-toluidine (0.461 mL, 4.25 mmol) and N-ethyldiisopropylamine (1.481 mL, 8.51 mmol) in CH3CN (30 mL) was heated under reflux for 3 h. The mixture was diluted with EtOAc, and was washed with brine and water. The organic extract was dried and concentrated under reduced pressure to give the title compound as a light yellow solid (1.2 g, 97%). [M+H] calc'd for C14H14N3ClO2, 292; found, 292.

Provenance & Evidence