Methyl iodide → HCID 86604625, compound

Participants

Reaction Steps

4-Chloro-5-hydroxy-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.4 g, 1.5 mmol) in tetrahydrofuran (10 mL) was slowly added to a slurry of sodium hydride (60 percent in mineral oil, 0.1 g 2.5 mmol) in tetrahydrofuran (30 mL) and stirred for one hour. Methyl iodide (2 mL) was added and the solution warmed to reflux for two hours. After cooling the reaction was quenched with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine, dried (NaSO4) and concentrated. The residue was purified by chromatography over silica (40 percent ethyl acetate/hexane) affording product as a yellow solid. (0.2 g, 50 percent) yield.

Provenance & Evidence