4-Chloropyridine hydrochloride → 2-(2-Methylpyrimidin-5-yl)-2-(pyridin-4-yl)acetonitrile

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Reaction Steps

A solution of 2-(2-methylpyrimidin-5-yl)acetonitrile (1.0 g, 7.51 mmol) and 4-chloropyridine hydrochloride (1.13 g, 7.51) in dioxane (20 mL) in a dried flask was degassed and filled with nitrogen. t-BuOK (18.8 mL, 1M in THF) was added. The mixture was stiffed at 100° C. for 4 h and cooled to room temperature, quenched by cooled sat. aq. NH4Cl (20 mL). The resulting mixture was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine (3×10 mL), dried over Na2SO4, concentrated under reduced pressure to give the crude product, which was purified by column chromatography on silica gel (MeOH: EtOAc=1:10) to give 2-(2-methylpyrimidin-5-yl)-2-(pyridin-4-yl)acetonitrile (700 mg, crude).

Provenance & Evidence