Diisopropylethylamine → 4-Chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile

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Reaction Steps

A dispersion of 0.5 g (2.3 mmol) of 4,6-dichloro-2-methylsulfanyl-pyrimidine-5-carbonitrile (J. Heterocycl. Chem. 1971, 8, 445-453) and 0.65 g (5.0 mmol) of N-ethyl-diisopropylamine in 40 ml of dioxane was treated at room temperature with 0.54 g (5.0 mmol) of 4-(4-fluorophenyl)-piperidine hydrochloride during 18 h. For the working-up, the reaction mixture was evaporated, and, thereafter, the residue obtained was directly chromatographed on silica gel using toluene as the eluent yielding 660 mg (1.8 mmol, 80% of theory) of 4-chloro-6-[4-(4-fluoro-phenyl)-piperidin-1-yl]-2-methylsulfanyl-pyrimidine-5-carbonitrile as an amorphous, white solid; MS: [M+H]+=363.

Provenance & Evidence