Tolylboronic acid → Methyl 2-(4-phenyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

Participants

Reaction Steps

methyl-2-(4-chloro-6-phenyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.031 g; 0.228 mmol), p-tolylboronic acid (0.031 g; 0.228 mmol), tetrakis(triphenylphosphine) palladium(0) (0.013 g; 0.011 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (0.75 mL) and water (0.25 mL). N,N-Diisopropylethylamine (0.060 mL; 0.344 mmol) was added, the tube was sealed and irradiated in a microwave oven at 130° C. for 30 min. The reaction mixture was partitioned between a solution of hydrochloric acid 1N and ethyl acetate. The phases were separated and the organic phase was washed with a 1N sodium bicarbonate solution and a saturated sodium chloride solution. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (0-10%) in heptane to give 0.018 g (45%) of the title compound.

Provenance & Evidence