HCID 86760395, compound → N-(4-Fluorophenyl)-2-(2-oxobutoxy)pyrimidine-5-carboxamide

Participants

Reaction Conditions

Reaction Steps

2-[(Methoxymethylcarbamoyl)methoxy]pyrimidine-5-carboxylic acid (4-fluorophenyl)amide (prepared as in Example 4, 60 mg, 0.18 mmol) was suspended in 1.8 mL THF and cooled to 0° C. Ethyl magnesium bromide (1 M in THF, 0.45 mL, 0.45 mmol) was added dropwise while maintaining internal reaction temperature between 0° C. and 5° C. The reaction mixture was warmed to ambient temperature and held for 1 h. The reaction mixture was cooled back to 0° C. and a second addition (0.45 mL, 0.45 mmol) of Grignard reagent was performed. The reaction was warmed to ambient temperature and held for 2.5 hours. The reaction was quenched with 0.1 M HCl and diluted with ethyl acetate. The organic layer was separated, dried using Na2SO4 and concentrated to 36 mg of yellow oil. The crude material was purified by SiO2 chromatography to deliver 8 mg (15% yield) of the titled compound. ESI-MS m/z 304 (MH+), 302 (M−H−).

Provenance & Evidence