2-Methoxyaniline → 4,6-Dichloro-N-(2-methoxyphenyl)-5-pyrimidinecarboxamide

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Reaction Steps

4,6-Dichloropyrimidine-5-carbonyl chloride (587 mg, 2.78 mmol, prepared according to E. V. Tarasov et al. Synlett 2000, 5, 625-626) was dissolved in dichloromethane (2.5 ml) and TEA (400 μl, 2.87 mmol) was added. To this solution, 2-methoxyaniline (340 mg, 2.76 mmol) in 3 ml DCM was added dropwise and the mixture was stirred for 30 min at room temperature. The reaction mixture was then diluted with dichloromethane, washed with 4% sodium bicarbonate solution, dried over magnesium sulphate, filtered and evaporated. After evaporation of the solvent, the residue was purified by flash chromatography using SP1® Purification System (10% to 40%, hexane-ethyl acetate) to obtain 630 mg (77% yield) of the title compound.

Provenance & Evidence