Benzenesulfonyl chloride → 5-Iodo-7-(phenylsulfonyl)-7H-Pyrrolo[2,3-d]pyrimidine

HRID 1403257ノート

反応式

HRID 1403257 の反応式
[I:1][C:2]1[C:10]2[CH:9]=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:13]1([S:19]([N:4]2[C:5]3[N:6]=[CH:7][N:8]=[CH:9][C:10]=3[C:2]([I:1])=[CH:3]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 106103365-Iodo-7H-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 579630495-Iodo-7-(phenylsulfonyl)-7H-Pyrrolo[2,3-d]pyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5-Iodo-7H-pyrrolo[2,3-d]pyrimidine (39, 0.569 g, 2.32 mmol) was added to 10.0 mL of N,N-dimethylformamide in a round bottom flask. Sodium hydride (0.102 g, 2.55 mmol) was added and the reaction stirred at room temperature for 10 minutes, then benzenesulfonyl chloride (40, 326 μL, 2.55 mmol) was added. The reaction was stirred at room temperature overnight, then poured into aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate adsorbed onto silica. The desired compound was isolated by silica gel column chromatography, eluting with 0.5-6% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum. Toluene was added to the residue, then concentrated under vacuum and the resulting solid was washed with hexane and collected by fitration to provide the desired compound (41, 439 mg). 1H NMR consistent with the compound structure.

後処理

  1. stirringThe reaction was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered

出典と根拠

ORDレコード
ord-9954d41ac9474fdda9a78cad265b6c30
出典データセット
uspto-grants-2014_12
特許番号
US08912204B2

反応ノート

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