Triethylamine → 5-Bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine

Participants

Reaction Steps

(Trimethylsilyl)acetylene (1.845 g, 2.655 mL, 18.78 mmol) was added dropwise to a solution of 3,5-dibromopyrazin-2-amine (5 g, 19.77 mmol), triethylamine (10.00 g, 13.77 mL, 98.85 mmol), Copper(I) iodide (451.7 mg, 2.372 mmol) and Pd(PPh3)4(1.142 g, 0.9885 mmol) in DMF (25.00 mL) and the resulting solution stirred at ambient temperature for 30 minutes. The reaction was diluted with EtOAc and water and the layers separated. The aqueous layer was extracted further with EtOAc and the combined organics washed with water, dried (MgSO4) and concentrated in vacuo. The mixture was purified on silica gel by flash column chromatography (0-15% EtOAc/Petrol) to afford the product as a yellow solid (3.99 g, 75% Yield). 1H NMR (400.0 MHz, DMSO) d 0.30 (s, 9H), 8.06 (s, 1H) ppm; MS (ES+) 271.82

Provenance & Evidence