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Dimethylformamide → 4-Methyl-4-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile

HRID 1501398
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HRID 1501398 반응식
CS(O[CH2:6][CH2:7][C:8]([CH3:24])([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)[CH3:9])(=O)=O.[CH3:25][N:26](C=O)C.[C-]#N.[Na+]>O>[CH3:9][C:8]([N:10]1[CH:14]=[C:13]([C:15]2[C:16]3[CH:23]=[CH:22][NH:21][C:17]=3[N:18]=[CH:19][N:20]=2)[CH:12]=[N:11]1)([CH3:24])[CH2:7][CH2:6][C:25]#[N:26]
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 57477613HCID 57477613, 화합물

생성물 1

HCID 177548084-Methyl-4-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]pentanenitrile수율 59%

시약·촉매·용매 1

HCID 962Water용매

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온도
125 °C

실험 절차

3-methyl-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butyl methanesulfonate (2.97 g, 8.50 mmol), DMF (120 mL) and sodium cyanide (6.21 g, 0.127 mol) were distributed evenly into six 20 mL microwavable vessels, each of which was heated in the microwave reactor for 4000 seconds at 125° C. The contents of the vials were combined and were diluted with 400 mL water and extracted with five 150 mL portions of ethyl acetate. The combined extracts were dried over sodium sulfate, and the solvent was removed in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (1.40 g, 59%).

후처리

  1. extractionextracted with five 150 mL portions of ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe crude residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-3dbf858f213a409f9ac8a4f343354ea4
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09206187B2

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