Trimethyl-2-propynylsilane → 5-Bromo-6-chloro-3-(3-(trimethylsilyl)prop-1-ynyl)pyrazin-2-amine

Participants

Reaction Steps

3,5-Dibromo-6-chloropyrazin-2-amine (step 1) (400 mg, 1.392 mmol) in dry THF (10 ml) was degassed with nitrogen and treated with trimethyl(prop-2-ynyl)silane (0.218 ml, 1.462 mmol), TEA (0.582 ml, 4.18 mmol), CuI (26.5 mg, 0.139 mmol) and Pd(PPh3)2Cl2 (98 mg, 0.139 mmol). After stirring at room temperature for 2 hours, the reaction mixture was diluted with water (100 ml) and brine and extracted with DCM (×3). The combined organic extracts were concentrated under reduced pressure. Purification of the crude product by chromatography on silica eluting with 0-20% EtOAc in iso-hexane afforded the titled compound;

Provenance & Evidence