Phosphorus oxychloride → Ethyl 4-chloropyrimidine-5-carboxylate

To a mixture of ethyl 3,4-dihydro-4-oxopyrimidine-5-carboxylate (3.54 g) (synthesized according to the method reported by A. R. Todd and F. Bergel on J. Chem. Soc., 364 (1937)) and triethylamine (2.13 g) was added dropwise under ice-cooling phosphorus oxychloride (21 ml), and the mixture was then heated for 1.5 hour under reflux. The reaction mixture was concentrated to dryness, which was poured into ice-water, followed by partitioning between chloroform and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and then dried. The solvent was distilled under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as a pale yellow oil (3.42 g, 86%).

1. customsynthesized
2. temperaturethe mixture was then heated for 1.5 hour
3. temperatureunder reflux
4. concentrationThe reaction mixture was concentrated to dryness, which
5. additionwas poured into ice-water
6. customby partitioning between chloroform
7. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
8. customdried
9. distillationThe solvent was distilled under reduced pressure
10. customThe residue was purified by column chromatography on silica gel

ORD record

ord-1376a1abb1bc4898a24a205e5329eb00

Source dataset

uspto-grants-1996_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05500427