2-(Tributylstannyl)pyrimidine → HCID 22961903, compound

Participants

Reaction Steps

To the solution of 5-bromo-6-chloro-3-(1-methyl-2-(R)-pyrrolidinylmethoxy)-pyridine (390 mg, 1.27 mmol) in toluene (15 mL) was added tetrekis(triphenylphosphine)palladium (40 mg, 1%) and tributyl(pyrimidinyl)tin (0.57 g, 1.53 mmol). The mixture was stirred and heated under reflux for 6 h. Solvent was evaporated and the residue was chromatographed (silica gel; CH2Cl2 /MeOH, 10:0.3 to 10:1) to afford an oil (193 mg, 50%): 1H NMR (CDCl3, 300 MHz) δ 1.62 (m, 1H), 1.68-1.90 (m, 2H), 2.02 (m, 1H), 2.32 (m, 1H), 2.50 (s, 3H), 2.70 (m, 1H), 3.12 (m, 1H), 3.98-4.06 (m, 2H), 7.25 (m, 1H), 8.18 (d, 1H, J=3.0 Hz), 8.87 (s, 2H), 9.29 (s, 1H); MS (CI/NH3) m/z 305 (M+H)+.

Provenance & Evidence