Ethyl Glycolate → Ethyl 2-pyrimidinyloxyacetate

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence