Dimethylformamide → HCID 68651269, compound

Participants

Reaction Steps

A mixture of 3-amino-6-bromopyrazine-2-cyclopropylcarboxamide (5.0 g, 19.4 mmole), [1,1′bis-(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (0.88 g, 1.9 mmol), 3-carbomethoxyphenylboronic acid (4.2 g, 23.3 mmol) in DMF (30 mL) was de-gassed with nitrogen. Triethylamine (5.4 mL, 38.9 mmol) was then added and the resulting mixture was heated at 85° for 2.5 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL), filtered over silica gel, washed with saturated sodium bicarbonate solution (150 mL), dried over sodium sulfate, filtered, and concentrated. The oily residue was purified by flash chromatography (silica gel, eluted with ethyl acetate-hexanes gradient from 15% to 80% yield) to give methyl 3-{5-amino-6-[(cyclopropylamino)carbonyl]pyrazin-2-yl}benzoate (a tan color solid, 4.5 g, 74% yield): 1H NMR (400 MHz, DMSO-d6): 8.67 (s, 1H), 8.50-8.49 (t, 1H), 8.07-8.03 (m, 2H), 7.57-7.54 (t, 1M), 3.98 (s, 3H), 2.91-2.88 (m, 1H), 0.94-0.85 (m, 2H), 0.72-0.62 (m, 2H); MS (EI) for C16H16N4O3: 428 (MH+).

Provenance & Evidence