Methyl iodide → HCID 20718796, compound

Participants

Reaction Steps

To a suspension of a 60% oil dispersion of NaH (96 mg, 2.2 mmol) in DMF (3 ml) at 0° C. was added a DMF solution (5 ml) of (+6-(3,4-Difluorophenyl)-2-methoxy-4-methyl-1,6-dihydro-pyrimidine-5-carboxylic acid methyl ester (592 mg, 2.0 mmol, [αD]=+28°). After the mixture was stirred 30 min, a DMF solution (2 ml) of methyliodide (312 mg, 2.2 mmol) was added and the reaction stirred at room temperature for 45 min. The DMF was removed in vacuo, the residue treated with water and extracted with ethyl acetate(3X). The extracts were combined, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give a crude oil (800 mg). Flash chromatography on silica gel (3% to 6% diethyl ether in methylene chloride) gave 6-(3,4-difluorophenyl)-2-methoxy-1,4-dimethyl-1,6-dihydro-pyrimidine-5-carboxylic acid methyl ester and 4-(3,4-difluorophenyl)-2-methoxy-1,6-dimethyl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester as colorless oils.

Provenance & Evidence