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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
ノート
印刷プレビュー

反応式

HRID 336137 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8b20a3e1ec6f4e0c872a46561ffaf299
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889666B2

反応ノート

読み込み中…

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