(E)-trimethyl(2-(tributylstannyl)vinyl)silane → HCID 68150547, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-amino-5-bromo-2-cyclopropylpyrimidine-4-carboxylate (0.5 g, 1.747 mmol, see WO 2005063721 for preparation) and tetrakis (triphenylphosphine) palladium(0) (0.214 g, 0.185 mmol) were added to a 20 mL Biotage microwave reaction vessel. The vessel was sealed and purged with nitrogen gas. (E)-trimethyl(2(tributylstannyl)vinyl)silane (0.96 g, 2.466 mmol) in dioxane (8.74 ml) was added and the reaction mixture was heated at 120° C. for 6 h. The cooled reaction mixture was diluted with ethyl acetate and water. The organic phase was washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated onto silica. Purification by flash chromatography (SiO2, 0-40% EtOAc:Hex gradient) provided the title compound as a tan solid (0.305 g, 57% yield): mp 99-101° C.; 1H NMR (400 MHz, DMSO-d6) δ 0.12 (s, 9H), 0.85-0.94 (m, 4H), 1.25 (t, J=7.1 Hz, 3H), 1.91 (tt, J=7.0, 5.6 Hz, 1H), 4.20 (q, J=7.1 Hz, 2H), 6.03 (d, J=19.1 Hz, 1H), 6.70 (d, J=19.2 Hz, 1H), 7.01 (s, 2H); ESIMS m/z 306 ([M+H]+), 304 ([M−H]−).

Provenance & Evidence