Water → HCID 67977685, compound

Participants

Reaction Steps

To a mixture of sodium hydride (60 wt % in mineral oil, 0.24 g, 6.0 mmol) in N,N-dimethylformamide (15 ml) at room temperature under nitrogen atmosphere was added a solution of tert-butyl 3-hydroxypiperidine-1-carboxylate (1.0 g, 5.0 mmol) in N,N-dimethylformamide (5 ml) dropwise. After the mixture was stirred for one hour, 2-chloro-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (1.1 g, 5.0 mmol) was added to the mixture. The resulting mixture was stirred overnight and poured into water. Extractive workup was performed with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. To the residue was added 4N hydrogen chloride in ethyl acetate (10 ml) and the resulting slurry was stirred at room temperature for 2 hours. After concentration under reduced pressure, the residue was dissolved in water. The aqueous solution was washed with ethyl acetate and basified with potassium carbonate. Extraction with chloroform was performed three times and the organic layer was dried over anhydrous sodium sulfate. After concentration, analytically pure 1-methyl-2-(piperidine-3-yloxy)-1H-[4,4′]bipyrimidinyl-6-one was isolated as a white solid (0.66 g, 2.3 mmol, 46%). This compound was used for the next reaction without further purification.

Provenance & Evidence