7-bromo-2,2-dimethyl-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one → 7-bromo-2,2-dimethyl-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazine

Temperature

0 °C

To a solution of 7-bromo-2,2-dimethyl-4H-pyrido[3,2-b][1,4]oxazin-3-one (0.360 g, 1.39 mmol) in THF (8.9 mL) at 0° C. was added BH3 (8.43 mL of a 1.0 M solution in THF, 8.43 mmol). The solution was heated to reflux. After 18 h, the solution was cooled to 0° C. and the reaction quenched with MeOH (15 mL). The mixture was concentrated and the resulting off-white solid was dissolved in MeOH (15 mL) and NaOH (10 mL of a 1 N solution). The mixture was heated at reflux to 4 h. The MeOH was removed under reduced pressure. The resulting precipitate was collected by filtration and washed with H2O (10 mL). The white solid was dried to give the title compound (0.260 g, 76%) as white needles: 1H NMR (300 MHz, DMSO-d6) δ 7.62 (d, J=2.1 Hz, 1H), 7.10 (d, J=1.5 Hz, 1H), 7.03 (br s, 1H), 3.14 (d, J=2.4 Hz, 2H), 1.25 (s, 6H); MS (ESI) m/e 243 (M+H)+.

1. temperatureThe solution was heated to reflux
2. customthe reaction quenched with MeOH (15 mL)
3. concentrationThe mixture was concentrated
4. dissolutionthe resulting off-white solid was dissolved in MeOH (15 mL)
5. temperatureThe mixture was heated
6. temperatureat reflux to 4 h
7. customThe MeOH was removed under reduced pressure
8. filtrationThe resulting precipitate was collected by filtration
9. washwashed with H2O (10 mL)
10. customThe white solid was dried

ORD record

ord-5e3455a78633483981ef2024ede36b51

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08450307B2