Hydrogen Bromide → 2-benzylpyrimidin-4(3H)-one

Temperature

95 °C

To a solution of 2-benzyl-4-methoxypyrimidine (0.675 g, 3.37 mmol) in AcOH (15 mL) was added HBr (2.28 mL, 20.2 mmol; 48 wt % in H2O). The reaction mixture was stirred at 95° C. for 2 hours. The reaction mixture was cooled to room temperature and diluted with H2O. The pH of the reaction mixture was adjusted to 5-6 with 6 M aqueous NaOH and then partitioned between EtOAc and H2O. The phases were separated, and the aqueous phase was re-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude yellow solid. Purification of the crude product was achieved by trituration with dichloromethane and diethyl ether. The resulting solid was filtered, washed with diethyl ether, collected and dried under vacuum to yield the desired product (0.531 g, 85%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.79 (d, J=6.6 Hz, 1H), 7.31 (m, 4H), 7.23 (m, 1H), 6.10 (d, J=6.6 Hz, 1H), 3.83 (s, 2H). LRMS (ESI pos) m/e 187 (M+1).

1. temperatureThe reaction mixture was cooled to room temperature
2. custompartitioned between EtOAc and H2O
3. customThe phases were separated
4. extractionthe aqueous phase was re-extracted with EtOAc (1×)
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customto yield a crude yellow solid
9. customPurification of the crude product
10. filtrationThe resulting solid was filtered
11. washwashed with diethyl ether
12. customcollected
13. customdried under vacuum

ORD record

ord-b0f74c2099ab49aa9ebcb0494fed6865

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003662B2