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

HRID 539060

반응식

HRID 539060 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:15]1[CH2:19][O:18][C:17](=[O:20])[NH:16]1)[CH2:13][CH3:14].[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:16]3[C@@H:15]([CH2:12][CH2:13][CH3:14])[CH2:19][O:18][C:17]3=[O:20])=[N:7][C:6]=12

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8063309AG-E-14754HCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

생성물 1

HCID 67034378(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-propyloxazolidin-2-one (0.354 g, 2.74 mmol) in dry DMF (10 mL) at ambient temperature was added sodium hydride (0.110 g, 2.74 mmol) and the solution was stirred for 18 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by normal phase column chromatography, eluting with 1-10% EtOAc/dichloromethane afforded 0.372 g (63%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one as a yellow solid.

후처리

  1. filtrationthe solids were collected by filtration
  2. customPurification of the crude material by normal phase column chromatography
  3. washeluting with 1-10% EtOAc/dichloromethane

출처 및 근거

ORD 기록
ord-e0476fbd87bc4675ab7a577312b0771f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865726B2

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