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Tetrabutylammonium Fluoride → 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol

HRID 2189326
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반응식

HRID 2189326 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([C:14]#[C:15][CH:16]([OH:18])[CH3:17])=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:14]=[C:15]([CH:16]([OH:18])[CH3:17])[N:8]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:6]=2[N:7]=1
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참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 866373494-[2-Chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol

생성물 1

HCID 735546611-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol수율 52.7%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-[2-chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol (0.23 g, 0.85 mmol) in THF (0.5 mL) is added 1M TBAF (4.3 mL). The reaction mixture is heated at reflux for 16 h, diluted with water, extracted with EtOAc. The extracts are dried over Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3) to provide 0.12 g of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanol.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts are dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3)

출처 및 근거

ORD 기록
ord-36f0704d68b54640ad4b8f0c8447139d
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08324225B2

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