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

HRID 1775161노트

반응식

HRID 1775161 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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 filtration to provide the desired compound (41, 439 mg). 1H NMR consistent with the compound structure.

후처리

  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

출처 및 근거

ORD 기록
ord-9be562949dfc4a4eab4dfaed8257a8ae
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260437B2

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