Benzyl Alcohol → 4-(Benzyloxy)-2-chloro-5-nitropyrimidine

Temperature

0 °C

Benzyl alcohol (5.57 g) was added to a suspension of sodium hydride (oil, 60%, 2.06 g) in DMF (100 mL) by small portions at 0° C., and the obtained mixture was stirred at 0° C. for 30 min. The reaction mixture was cooled to 0° C., 2,4-dichloro-5-nitropyrimidine (10.0 g) was added thereto, and the obtained mixture was stirred at 0° C. for 1 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (670 mg). 1H NMR (300 MHz, DMSO-d6) δ 5.62 (2H, s), 7.24-7.73 (5H, m), 9.28 (1H, s).

1. temperatureThe reaction mixture was cooled to 0° C.
2. stirringthe obtained mixture was stirred at 0° C. for 1 hr
3. extractionthe mixture was extracted with ethyl acetate
4. washThe combined organic layer were washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-4f58860f7f94438b9cf503d061802f47

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133129B2