Ethyl Glycolate → Ethyl 2-pyrimidinyloxyacetate

Temperatur

0 °C

To a slurry of sodium hydride (60% dispersion in mineral oil), 280 mg (5.76 mmol) in 10 mL of DMF at 0° C. was added 0.52 mL (4.8 mmol) of ethyl glycolate. After 10 minutes, 0.92 g (5.76 mmol) of 2-bromopyrimidine was added. The reaction mixture was stirred 15 min at 0° C. then ice bath was removed. After four hours, reaction mixture was quenched with methanol and concentrated to dryness. The residue was partitioned between 20% isopropanol/chloroform and water, then extracted with 20% isopropanol/chloroform. The combined organics were washed with saturated aqueous sodium bicarbonate, washed with brine, dried over sodium sulfate, filtered, and concentrated to dryness. The residue was purified by radial chromatography using a methanol/chloroform gradient as eluent and concentrated to dryness to yield 0.45 g (52%) of the desired product as a colorless oil. MS (ion spray) 183.1 (M+1).

1. customice bath was removed
2. waitAfter four hours
3. customreaction mixture
4. customwas quenched with methanol
5. concentrationconcentrated to dryness
6. customThe residue was partitioned between 20% isopropanol/chloroform and water
7. extractionextracted with 20% isopropanol/chloroform
8. washThe combined organics were washed with saturated aqueous sodium bicarbonate
9. washwashed with brine
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated to dryness
13. customThe residue was purified by radial chromatography
14. concentrationconcentrated to dryness

ORD-Eintrag

ord-5ed76f0874ef4619876da29748eb86df

Quelldatensatz

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06743794B2