Potassium tert-butoxide → 2-bromo-5H-pyrrolo[2,3-b]pyrazine

Participants

Reaction Conditions

Reaction Steps

Potassium tert-butoxide (6.612 g, 58.92 mmol) was suspended/dissolved in dry N-methylpyrrolidinone (15 mL) and stirred at 80° C. while a solution of 5-bromo-3-(2-triethylsilylethynyl)pyrazin-2-amine (9.1992 g, 29.46 mmol) in dry N-methylpyrrolidinone (50 mL) was added slowly drop wise over 10 minutes. The dropping funnel was washed out with a further aliquot of dry N-methylpyrrolidinone (10 mL). The resultant was stirred at 80° C. for 1.5 hours. Reaction mixture cooled to ambient then diluted with EtOAc and water and EtOAc layer washed with small portions of water (×6). Organic layer dried (MgSO4), filtered and concentrated in vacuo to give a dark brown solid (4.1 g, 70.3%). 1H NMR (400.0 MHz, DMSO) δ 12.50 (s, 1H), 8.37 (s, 1H), 8.01 (s, 1H) and 6.64 (q, J=1.7 Hz, 1H) ppm; MS (ES+) 198.10.

Provenance & Evidence