2,6-Dimethylaniline → 2,4-Dichloro-N-(2,6-dimethylphenyl)pyrimidine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 20.3 g (96 mmol) of 2,4-dichloropyrimidine-5-carbonyl chloride 29 and Amberlyst A21 (2.1 g) in 400 mL of EtOAc was added dropwise 11.7 mL of 2,6-dimethylaniline (95 mmol) at room temperature. The resulting mixture was heated to 50° C. for 12 h, and then was filtered. The filtrate was washed sequentially with water (200 mL), 1N HCl (50 mL), 1N NaOH (50 mL), and brine (100 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was washed with a small amount of DCM to give the title compound as a white solid. Mass Spectrum (ESI) m/e=297.1 (M+1).

Provenance & Evidence