Cesium carbonate → tert-butyl 3-(2-chloropyrimidin-4-yloxy)azetidine-1-carboxylate

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Reaction Conditions

Reaction Steps

A flask was charged with a solution of 2,4-dichloropyrimidine (300 mg, 2.0 mmol) in N,N-dimethylformamide (10 mL). tert-Butyl 3-hydroxyazetidine-1-carboxylate (349 mg, 2.0 mmol) and cesium carbonate (1.11 g, 3.42 mmol) were added and the resulting mixture was heated to 80° C. for 2 h. Upon completion, the mixture was diluted with ethyl acetate (20 mL) and washed with 1:1 water:brine (3×40 mL). The organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by Chromatography on silica gel (0-80% ethyl acetate in hexanes) afforded tert-butyl 3-[(2-chloropyrimidin-4-yl)oxy]azetidine-1-carboxylate (550 mg, 1.9 mmol, 96%). MS ESI: [M+H]+ m/z 286.1.

Provenance & Evidence