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Triacetoxyperiodinane → 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanone

HRID 2189327
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HRID 2189327 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11]([OH:13])[CH3:12])[N:8]([CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[C:6]=2[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11](=[O:13])[CH3:12])[N:8]([CH:14]([CH2:15][CH3:16])[CH2:17][CH3:18])[C:6]=2[N:7]=1
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참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 735546611-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol

생성물 1

HCID 735546581-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanone수율 109.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanol (61 mg, 0.2 mmol) in CH2Cl2 (2 mL) is added Dess-Martin periodinane (242 mg, 0.5 mmol). The reaction mixture is stirred for 1 h, quenched with 10% NaS2O3:saturated NaHCO3 (1:1) aqueous solution, and extracted with CH2Cl2. The extracts are washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3) to afford 58 mg of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanone.

후처리

  1. customquenched with 10% NaS2O3
  2. extractionsaturated NaHCO3 (1:1) aqueous solution, and extracted with CH2Cl2
  3. washThe extracts are washed with water and brine
  4. dry with materialdried 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-d0b104fe8ec845cf86ae85f1f0c6d40c
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08324225B2

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