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Tetrabutylammonium Fluoride → (1-methyl-cyclopropyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

HRID 1677391
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HRID 1677391 반응식
[CH3:1][C:2]1([C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[N:14]=3)[N:9]([Si](C(C)C)(C(C)C)C(C)C)[CH:8]=2)=[O:6])[CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:1][C:2]1([C:5]([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([C:16]4[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=4)[N:14]=3)[NH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3]1
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참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 67342981(1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone

생성물 1

HCID 44206485(1-methyl-cyclopropyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone수율 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (1-methyl-cyclopropyl)-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone (20 mg, 0.4 mmol) in anhydrous tetrahydrofuran (2 ml) was treated with tetrabutyl ammonium fluoride (1M in tetrahydrofuran, 0.1 ml, 0.1 mmol) dropwise. The reaction mixture was allowed to stir at room temperature for 10 minutes, and then partitioned between EtOAc/water. The organic layers were collected, dried over MgSO4, filtered, and concentrated giving a yellow solid. The residue was purified by preparative thin layer chromatography using 70% EtOAc in hexanes as eluant to provide 10 mg (71%) of (1-methyl-cyclopropyl)-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-methanone as a white solid. M+H=368.

후처리

  1. custompartitioned between EtOAc/water
  2. customThe organic layers were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving a yellow solid
  7. customThe residue was purified by preparative thin layer chromatography

출처 및 근거

ORD 기록
ord-1308c7d92bde4a39a19563aad6402c27
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008298B2

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