4-Toluenesulfonyl chloride → 5-Bromo-4-Chloro-7-Tosyl-7H-Pyrrolo[2,3-D]Pyrimidine

HRID 1750254

반응식

HRID 1750254 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Br:12][C:13]1[C:21]2[C:20]([Cl:22])=[N:19][CH:18]=[N:17][C:16]=2[NH:15][CH:14]=1.[OH-].[Na+]>CC(C)=O.O>[Br:12][C:13]1[C:21]2[C:20]([Cl:22])=[N:19][CH:18]=[N:17][C:16]=2[N:15]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:14]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

생성물 1

HCID 577502825-Bromo-4-Chloro-7-Tosyl-7H-Pyrrolo[2,3-D]Pyrimidine

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

4-Methylbenzenesulfonyl chloride (5.21 g, 27.3 mmol) was added to a suspension of 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (6.34 g, 27.3 mmol) in acetone (70 mL). After addition of an aqueous solution of sodium hydroxide (1.11 g, 27.8 mmol in 15 mL water), the reaction mixture was stirred at room temperature for 16 hours. The mixture was then diluted with water (125 mL), stirred for 10 minutes, and filtered. The collected solids were washed with water to afford the product as a solid, Yield: 8.88 g, 23.0 mmol, 84%. LCMS m/z 385.9, 387.9, 389.8 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 8.84 (s, 1H), 8.42 (s, 1H), 8.06 (br d, J=8.4 Hz, 2H), 7.46-7.51 (m, 2H), 2.37 (br s, 3H).

후처리

  1. stirringstirred for 10 minutes
  2. filtrationfiltered
  3. washThe collected solids were washed with water

출처 및 근거

ORD 기록
ord-76d34c1edc30447f81a8dc09cafb5ffe
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156845B2

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