Bromine → 2-benzyl-5-bromopyrimidin-4(3H)-one

To a solution of 2-benzylpyrimidin-4(3H)-one (0.531 g, 2.85 mmol) in CHCl3 (15 mL) and methanol (3 mL) was added bromine (0.146 mL, 2.85 mmol). The reaction mixture was stirred at room temperature for 3 hours and then quenched with 10% sodium bisulfite solution. The reaction mixture was 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. The resulting solid was filtered, washed with dichloromethane, collected and dried under vacuum to yield the desired product (0.302 g, 40%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.23 (br s, 1H), 8.25 (s, 1H), 7.35-7.28 (m, 4H), 7.27-7.22 (m, 1H), 3.87 (s, 2H). LRMS (ESI pos) m/e 265, 267 (M+1, Br pattern).

1. customquenched with 10% sodium bisulfite solution
2. customThe reaction mixture was partitioned 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 dichloromethane
12. customcollected
13. customdried under vacuum

ORD record

ord-2cf881220cc842ffb39a14923a131b16

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003662B2