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Sodium hydride → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one

HRID 539064
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반응식

HRID 539064 반응식
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8](Cl)=[N:7][C:6]=12.[CH2:12]([C@H:14]1[CH2:18][O:17][C:16](=[O:19])[NH:15]1)[CH3:13].[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:15]3[C@@H:14]([CH2:12][CH3:13])[CH2:18][O:17][C:16]3=[O:19])=[N:7][C:6]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7832546(S)-4-ethyloxazolidin-2-oneHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

생성물 1

HCID 67033956(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one수율 56.3%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (0.375 g, 1.61 mmol) and (S)-4-ethyloxazolidin-2-one (0.279 g, 2.42 mmol) in DMF (10 mL) was added sodium hydride (0.0968 g, 2.42 mmol) at ambient temperature. The mixture was stirred for 18 hours. Saturated aqueous NH4Cl was added and the solids were collected by filtration. Purification of the crude material by column chromatography (1-10% EtOAc in DCM) provided (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one (0.282 g, 56% yield) as a pale yellow solid.

후처리

  1. filtrationthe solids were collected by filtration
  2. customPurification of the crude material by column chromatography (1-10% EtOAc in DCM)

출처 및 근거

ORD 기록
ord-efb800951b63423b9528848313f9d9e4
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08865726B2

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