(E)-trimethyl(2-(tributylstannyl)vinyl)silane → HCID 70497062, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 6-amino-2-(4-chloro-2-fluorophenyl)-5-iodopyrimidine-4-carboxylate (400 mg, 0.981 mmol) and tetrakis(triphenylphosphine)palladium(0) (113 mg, 0.098 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 (497 mg, 1.276 mmol) in dioxane (4907 μl) was added and the reaction mixture was stirred overnight at 90° C. under nitrogen. 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, 0-20% EtOAc:Hex gradient) provided the title compound as a tan solid (0.283 g, 76% yield): 1H NMR (400 MHz, DMSO-d6) d 0.16 (s, 9H), 3.78 (s, 3H), 6.14 (d, J=19.1 Hz, 1H), 6.80 (d, J=19.1 Hz, 1H), 7.21-7.68 (m, 4H), 7.92 (t, J=8.4 Hz, 1H); 19F NMR (376 MHz, DMSO-d6) d −110.46; ESIMS m/z 380 ([M+H]+), 378 ([M−H]−).

Provenance & Evidence