Dichloromethane → HCID 69558084, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 82 mg (3.43 mmol) of sodium hydride in 4 mL of benzene was added 315 mg (3.43 mmol) of methyl glycolate and a solution of 384 mg (1.14 mmol) of 2-(methylthio)-4-chloro-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidine in 4 ml of benzene. The mixture was heated at 57° C. and monitored by TLC (silica, methylene chloride) for conversion to product. After 2 days, the reaction was cooled to ambient temperature and partitioned by the addition of 15 mL of 2 M sodium hydrogen sulfate and 15 mL of ethyl acetate. The aqueous phase was extracted twice with 7 mL portions of ethyl acetate. The combined organic phases were dried with sodium sulfate and concentrated 600 mg of solid. The product was purified by flash chromatography (54 g silica, hexane-ethyl acetate gradient 100:0 to 75:25) to provide 211 mg (48%) of [[2-(methylthio)-6-ethyl-7-[(3-fluorophenyl)methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]acetic acid methyl ester as a white solid. nmr (300 MHz, CDCl3) δ1.14 (t, 3H), 2.53 (s, 3H), 2.55 (q, 2H), 3.88 (s, 3H), 5.04 (s, 2H), 5.36 (s, 2H), 6.30 (s, 1H), 6.75 (d, 1H), 6.85 (d, 1H), 6.96 (dt, 1H), 7.26 (dt, 1H)

Provenance & Evidence