Tolylboronic acid → Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of mixture of methyl 2-(2,4-dichloro-6-methylpyrimidin-5-yl)pentanoate (2.56 g, 7.18 mmol) in a degassed mixture of 1,2-dimethoxyethane-water (3:1, 60 mL) were added p-tolylboronic acid (1.51 g; 10.77 mmol), tetrakis(triphenylphosphine)palladium (0.846 g; 0.732 mmol) and diisopropylethylamine (5 mL; 28.70 mmol). The resulting mixture was heated at 90° C. for 2 h. After cooling, the reaction mixture was partitioned between brine and ethyl acetate, the phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (3-20%) in heptane furnished 0.935 g (27%) of the title compound as an oil.

Provenance & Evidence