4,6-Dichloropyrimidine → tert-Butyl 4-[(6-chloropyrimidin-4-yl)oxy]piperidine-1-carboxylate

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Reaction Steps

To a solution of 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (3.1 g, 15.5 mmol) and potassium tert-butoxide (1.74 g, 1 eq) in 20 mL THF at 0° C., was added 4,6-dichloropyrimidine (2.3 g, 1 eq). The reaction mixture was stirred for 1 h then a solution of saturated sodium bicarbonate was added. The aqueous layer was extracted with ethyl acetate twice and the combined extracts were washed with a solution of saturated sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue was purified on silica gel (eluent: 20% ethyl acetate in hexane) to give 2.49 g (51% yield) of 3a.

Provenance & Evidence