反应详情

温度

100 °C

A resealable tube was charged with (S)-3-(4-(2-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.034 g, 0.077 mmol), dioxane (2.0 mL), and water (0.667 mL). Concentrated HCl (37%) (0.167 mL) was added, the system was flushed with argon, the tube was sealed, and the reaction mixture was stirred at 100° C. for 1.5 hours. The reaction mixture was next partitioned between EtOAc and saturated aqueous NaHCO3 solution. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl)phenyl)-4-phenyloxazolidin-2-one (0.034 g, 0.078 mmol, 100% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (s, 3H), 1.65 (s, 3H), 5.48 (s, 1H), 7.18-7.45 (m, 6H), 7.48-7.59 (m, 2H), 7.65-7.75 (m, 2 H), 8.32 (d, J=2.45 Hz, 1H), 8.43 (d, J=2.54 Hz, 1H), 8.80 (d, J=4.89 Hz, 2H), 12.13 (br. s., 1H). m/z (ESI) 439 (M+H)+.

1. customthe system was flushed with argon
2. customthe tube was sealed
3. customThe reaction mixture was next partitioned between EtOAc and saturated aqueous NaHCO3 solution
4. extractionThe aqueous phase was extracted with EtOAc
5. washThe combined organic phases were washed with brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated