Methyl Glycolate → [5-(4-Fluorophenylcarbamoyl)pyrimidin-2-yloxy]acetic acid methyl ester

Participants

Reaction Steps

To a solution of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (prepared as in Example 1, 150 mg, 0.535 mmol) in THF (2 mL) was added methyl glycolate (82.5 μL, 1.07 mmol) followed by DBU (160 μL, 1.07 mmol). The reaction was stirred for 5 h, diluted with 3/6/1 ethyl acetate/hexane/dichloromethane, and passed through a plug of SiO2 using 4/5/1 ethyl acetate/hexane/dichloromethane. The filtrate was concentrated, and the resulting solids triturated with dichloromethane/hexane to afford 95.1 mg (58% yield) of the titled ester as a white solid. ESI-MS m/z 306 (MH+), 304 (M−H)−.

Provenance & Evidence