N,N'-Dimethylethylenediamine → (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)pyridin-1 (2H)-yl)phenyl)-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (S)-3-(4-iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (Intermediate C)(0.100 g, 0.254 mmol), 5-(pyrimidin-2-yl)pyridin-2(1H)-one (0.048 g, 0.280 mmol), tribasic potassium phosphate (0.270 g, 1.272 mmol) and dioxane (2.5 mL). The mixture was purged with argon and then copper (I) iodide (0.048 g, 0.254 mmol) and N,N′-dimethylethylenediamine (0.055 mL, 0.509 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 4 hours in the microwave. The reaction mixture was then filtered through Celite® brand filter aid and the filtrate was concentrated to afford a green solid. The resulting green solid was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)pyridin-1 (2H)-yl)phenyl)-4-phenyloxazolidin-2-one (0.078 g, 0.178 mmol, 70% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.66 (s, 3H), 5.52 (s, 1H), 6.60 (dd, J=9.59, 0.59 Hz, 1H), 7.21-7.53 (m, 8H), 7.59-7.71 (m, 2H), 8.36 (dd, J=9.63, 2.59 Hz, 1H), 8.43-8.53 (m, 1H), 8.79 (d, J=4.89 Hz, 2H). m/z (ESI) 439 (M+H)+.

Provenance & Evidence