Diisopropylethylamine → N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-2-(pyridin-2-ylmethoxy)pyrimidine-5-carboxamide

Participants

Reaction Steps

To a solution of 2-(methylthio)pyrimidine-5-carboxylic acid (1.50 g, 8.82 mmol) and 3-amino-N-cyclopropyl-4-methylbenzamide (1.68 g, 8.82 mmol) in DMF (7.5 mL) was added HATU (3.69 g, 9.70 mmol) and DIPEA (4.30 mL, 26.46 mmol) and the resulting mixture stirred for 16 h at room temperature. Saturated aqueous sodium bicarbonate was added and the mixture extracted with ethyl acetate, washed with brine and concentrated under reduced pressure to give the title compound as a solid (3.04 g, 100%); NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.69 (m, 2H), 2.28 (s, 3H), 2.60 (s, 3H), 2.86 (m, 1H), 7.36 (m, 1H), 7.65 (m, 1H), 7.85 (m, 1H), 8.39 (m, 1H), 9.12 (s, 2H), 10.18 (m, 1H); Mass Spectrum: M−H′ 341.

Provenance & Evidence