Triethylamine → HCID 68651837, compound

Participants

Reaction Conditions

Reaction Steps

The intermediate 3-amino-N-(2-hydroxyethyl)-6-bromopyrazine-2-carboxamide (108 mg, 0.4 mmole), [1,1′bis-(diphenylphosphino)ferrocene]dichloropalladium(II)-dichloromethane complex (19 mg, 0.04 mmol), 3-methylphenylboronic acid (67 mg, 0.5 mmol) in DMF (2 mL) was de-gassed with nitrogen. Triethylamine (0.12 mL, 0.8 mmol) was then added and the resulting mixture was heated at 85° C. for 2.5 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (10 mL), filtered over silica gel, washed with saturated sodium bicarbonate solution (10 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-amino-N-(2-hydroxyethyl)-6-(3-methylphenyl)pyrazine-2-carboxamide as a solid: (95 mg, 84% yield): 1H NMR (400 MHz, DMSO-d6): 8.78 (s, 1H), 8.78-8.61 (b, 1H), 7.89 (s, 1H), 7.49-7.52 (t, 1H), 7.51-7.49 (d, 1H), 7.14-7.12 (d,1H), 3.50-3.35 (m, 2H), 2.89-70 (m, 2H), 2.51 (s, 3H): MS (EI) for C14H16N4O2: 273 (MH+).

Provenance & Evidence