2-(Tributylstannyl)pyrimidine → 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-(5-pyrimidiny)pyridine

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Reaction Steps

To the solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (670 mg, 1.88 mmol) in toluene (10 mL) was added tetrekis(triphenylphosphine)palladium (70 mg, 1%) and tributyl(pyrimidinyl)tin (0.84 g, 2.26 mmol). The mixture was stirred and heated under reflux for 16 h. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtOAc, 10:1 to 2:1) to afford an oil (473 mg, 71%): 1H NMR (CDCl3, 300 MHz) δ 1.44 (s, 9H), 1.88-2.00 (m, 2H), 2.05 (m, 1H), 3.30-3.48 (m, 2H), 4.04 (m, 1H), 4.10-4.22 (m, 2H), 4.30 (m, H), 7.64 (s, 1H), 8.42 (d, 1H, J=2.5 Hz), 8.45 (s, 1H), 8.98 (br s, 1H), 9.01 (s, 1H), 9.27 (s, 1H); MS (CI/NH3) m/z 357 (M+H)+.

Provenance & Evidence