Sodium hydride → tert-Butyl 4-((2-chloropyrimidin-4-yl)oxy)piperidine-1-carboxylate

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Reaction Steps

tert-Butyl 4-hydroxypiperidine-1-carboxylate (500 mg, 2.48 mmol) was added to a suspension of sodium hydride (60%, 149 mg, 3.73 mmol) in THF (8.28 mL) and the mixture was stirred for 30 minutes at room temperature. 2,4-Dichloropyrimidine (333 mg, 2.24 mmol) was added to the reaction mixture at 0° C. and warmed to room temperature over 3 days. The mixture was diluted with ethyl acetate (20.0 mL), and then washed with water:brine 1:1 (3×40 mL). The organic extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (10-60% ethyl acetate in hexanes) to yield tert-butyl 4-[(2-chloropyrimidin-4-yl)oxy]piperidine-1-carboxylate. MS APCI calc'd for C14H21ClN3O3 [M+H]+ 314. found 314.

Provenance & Evidence