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

Participants

Reaction Steps

methyl 2-(4-chloro-6-ethyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (0.190 g; 0.559 mmol), p-tolylboronic acid (114 mg; 0.839 mmol), tetrakis(triphenylphosphine) palladium(0) (64.6 mg; 0.056 mmol) were placed in a 5 mL reaction tube and dissolved in a mixture of degassed DME (1.50 mL) and water (0.5 mL). N,N-Diisopropylethylamine (0.344 mL; 2.236 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 brine and dichloromethane, filtered over a phase separator filter (1PS) and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane to give 85 mg (35%) of the title compound as a yellow oil.

Provenance & Evidence