Benzenesulfonyl chloride → 4-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

HRID 398223노트

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HRID 398223 반응식
[H-].[Na+].[Cl:3][C:4]1[C:5]2[CH:12]=[CH:11][NH:10][C:6]=2[N:7]=[CH:8][N:9]=1.[H][H].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.O>[C:15]1([S:21]([N:10]2[C:6]3[N:7]=[CH:8][N:9]=[C:4]([Cl:3])[C:5]=3[CH:12]=[CH:11]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 109463064-Chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

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온도
0 °C

실험 절차

In a flame-dried flask under nitrogen, 780 mg of 60% sodium hydride (19.5 mmol) in mineral oil was added to 30 mL of dimethylformamide (DMF) and the resulting mixture cooled to 0° C. A solution of 2.0 g (13.0 mmol) of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine in 10 mL of DMF was added slowly over a 5 min period. The reaction was stirred for 10 min at which time generation of hydrogen (H2) ceased. Benzenesulfonylchloride (1.7 mL/13.0 mmol) was added, the reaction warmed to room temperature and stirred for 1 h. Water was added, and the resulting precipitate was filtered and dried in vacuo to obtain 3.4 g (89%) of the title compound as a crystalline solid, mp 163-167° C.

후처리

  1. temperaturethe reaction warmed to room temperature
  2. filtrationthe resulting precipitate was filtered
  3. customdried in vacuo

출처 및 근거

ORD 기록
ord-d504e83546a94d11a30ffd1cf0b6d847
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610847B2

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