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N-bromobutanimide → 6-bromo-7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 336137
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인쇄 미리보기

반응식

HRID 336137 반응식
[Br:1]N1C(=O)CCC1=O.[Si:9]([O:16][CH:17]([CH:39]=[CH2:40])[CH2:18][N:19]1[C:23]2[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=2[C:21]([C:29]2[CH:30]=[N:31][C:32]3[C:37]([CH:38]=2)=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:20]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:20]1[N:19]([CH2:18][CH:17]([O:16][Si:9]([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11])[CH:39]=[CH2:40])[C:23]2[N:24]=[CH:25][N:26]=[C:27]([NH2:28])[C:22]=2[C:21]=1[C:29]1[CH:30]=[N:31][C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 867112787-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

생성물 1

HCID 867112776-bromo-7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine수율 90.1%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

N-Bromosuccinimide (894 mg) was added to a solution of 7-(2-(tert-butyldimethylsilyloxy)-3-butenyl)-5-(quinolin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (2.13 g) obtained in Step 5 in DMF (25 ml) at room temperature. After stirring at the same temperature for 30 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a yellow solid (2.26 g).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8b20a3e1ec6f4e0c872a46561ffaf299
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08889666B2

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