Sodium Carbonate → HCID 89813784, compound

Participants

Reaction Conditions

Reaction Steps

2-Chloropyrimidine-4-carbonitrile (22.42 mg, 0.161 mmol), Na2CO3 (134 μL, 0.268 mmol), (S)-3-(4-(6-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (65 mg, 0.134 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (10.94 mg, 0.013 mmol) were combined in dioxane (268 μL) and stirred at 100° C. in a microwave oven for 1 hour. LC-MS indicated good conversion to desired product. After cooling to room temperature, the reaction mixture was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 10% MeOH in DCM, to provide (S)-2-(2-amino-5-(4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)phenyl)pyridin-3-yl)pyrimidine-4-carbonitrile as yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.83 (d, J=4.70 Hz, 1H), 8.59 (d, J=2.67 Hz, 1H), 8.13 (d, J=8.44 Hz, 1H), 8.06 (dd, J=2.14, 6.30 Hz, 1H), 7.66 (d, J=8.66 Hz, 2H), 7.58 (d, J=8.87 Hz, 2H), 7.49 (d, J=4.49 Hz, 1H), 7.35-7.42 (m, 2H), 7.23-7.35 (m, 3H), 5.49 (s, 1H), 1.66 (s, 3H), 0.92 (s, 3H). m/z (ESI) 463.8 (M+H)+.

Provenance & Evidence