Water → 5-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine

HRID 1192354노트

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HRID 1192354 반응식
[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[C:14]1([S:20]([N:4]2[C:5]3[N:6]=[CH:7][N:8]=[C:9]([Cl:11])[C:10]=3[C:2]([Br:1])=[CH:3]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 224845355-Bromo-4-chloro-7-(phenylsulfonyl)-7H-pyrrolo[2,3-D]pyrimidine수율 101.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of 5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 13 mmol) in DMF (40 mL) at 0° C. was added NaH (60% w/w in mineral oil, 720 mg, 18.1 mmol) and the mixture stirred at 0° C. under N2 for 30 minutes. Then PhSO2Cl (1.7 g, 13 mmol) was added and the reaction stirred at room temperature for 2 hours, after which H2O (200 mL) was added, causing precipitation. The precipitate was collected by filtration and dried under vacuum to give 7-Benzenesulfonyl-5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (4.9 g, 100%.) 1H NMR (DMSO-d6, 400 MHz) δ 8.85 (1H, s), 8.45 (1H, s), 8.19 (2H, d, J 8.7 Hz), 7.81 (1H, t, J 7.4 Hz), 7.70 (2H, t, J 7.8 Hz.)

후처리

  1. stirringthe reaction stirred at room temperature for 2 hours
  2. customprecipitation
  3. filtrationThe precipitate was collected by filtration
  4. customdried under vacuum

출처 및 근거

ORD 기록
ord-3e3e6868402a4d3ab040d46446b965f2
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680114B2

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