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

HRID 1750254

Reaktionsgleichung

Reaktionsgleichung von HRID 1750254
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-76d34c1edc30447f81a8dc09cafb5ffe
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156845B2

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