Réaction #1552136

Équation de réaction

tert-butyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate

sodium hydride

cyclobutanol

→

title compound

Rendement 88.0%

tert-butyl 4-(6-cyclobutoxypyrimidin-4-yl)piperazine-1-carboxylate

Rendement 88.0%

Solvants

DMF

DMF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was stirred at rt for 12 h
2. 2
   workup.ADDITIONThen, the mixture was poured onto water
3. 3
   Extractionthe aqueous layer was extracted with EtOAc (twice)
4. 4
   SéchageThe combined organic layer was dried over sodium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (5:1-3:1)

Mode opératoire

To a suspension of sodium hydride (60% in mineral oil, 469 mg, 11.7 mmol) in DMF (15 mL) was added cyclobutanol (0.92 ml, 11.7 mmol) at 0° C. After stirring at 0° C. for 30 min, a solution of tert-butyl 4-(6-chloropyrimidin-4-yl)piperazine-1-carboxylate (700 mg, 2.34 mmol) in DMF (0.5 mL) was slowly added, and the mixture was stirred at rt for 12 h. Then, the mixture was poured onto water, and the aqueous layer was extracted with EtOAc (twice). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (5:1-3:1) to give 687 mg (88% yield) of the title compound as a white solid.

Source