Boron tribromide → 2-(4-(4-Chloro-2-hydroxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) stirred solution of methyl 2-(4-(4-chloro-2-methoxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.125 mg; 0.294 mmol) in dichloromethane (1.5 mL) was added a solution of boron tribromide (1M in dichloromethane) (0.340 mL; 0.340 mmol) dropwise. After 1 h the mixture was allowed to warm up to room temperature and the reaction was stirred for 16 h. The reaction was quenched by adding water and the mixture was extracted with ethyl acetate, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purifications by flash-chromatography on silica gel using a gradient of methanol (0-10%) in dichloromethane and by preparative TLC on silica gel using a mixture methanol-dichloromethane (5:95) as eluent furnished 0.0018 g (1.5%) of the title compound.

Provenance & Evidence