Sodium hydride → Tert-butyl 4-(6-cyclobutoxypyrimidin-4-yl)piperazine-1-carboxylate

Temperatur

0 °C

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.

1. stirringthe mixture was stirred at rt for 12 h
2. additionThen, the mixture was poured onto water
3. extractionthe aqueous layer was extracted with EtOAc (twice)
4. dry with materialThe combined organic layer was dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by column chromatography on silica gel eluting with hexane/EtOAc (5:1-3:1)

ORD-Eintrag

ord-7e75f1c1ea534cc7bfccb30e6bf5a591

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08999974B2