N,N,N',N'-Tetramethylethylenediamine → 4-Methyl-6-(4-(1-(5-methylpyrazin-2-yl)piperidin-4-yl)piperidin-1-yl)pyrimidine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

The 1-(2-chloro-6-methylpyrimidin-4-yl)-1′-(5-methylpyrazin-2-yl)-4,4′-bipiperidine (700 mg, 1.8 mmol) was placed in a pressure tube and anhydrous toluene (4 mL) added. To the stirred solution was added: palladium(II) acetate (41 mg, 0.18 mmol), 1,5-bis(dipenylphosphino)pentane (159 mg, 0.36 mmol), N,N,N′,N′-tetramethylethylenediamine (0.11 mL, 0.724 mmol), and potassium cyanide (235 mg, 3.62 mmol). The vessel was degassed with N2, sealed and heated at 140° C. for 16 hours. The mixture was allowed to cool to r.t., diluted with ethyl acetate (50 mL), washed with brine (10 mL×1), dried over magnesium sulfate, filtered and concentrated in vac. The residue was purified by chromatography on silica gel with 20% acetone: hexanes to yield the title compound.

Provenance & Evidence