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

HRID 423078

Reaktionsgleichung

Reaktionsgleichung von HRID 423078
[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.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[Na+]>CC(C)=O>[Br:1][C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([S:18]([C:15]2[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=2)(=[O:20])=[O:19])[CH:3]=1

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53807105-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine2×

Produkt 1

HCID 577502825-Bromo-4-Chloro-7-Tosyl-7H-Pyrrolo[2,3-D]PyrimidineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

5-Bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (Intermediate 50) (2 g, 8.60 mmol) and p-toluenesulfonyl chloride (1.640 g, 8.60 mmol) was taken up in acetone (12 mL) and stirred under nitrogen and cooled to between −5° C. and 5° C. To this solution was added 2.0M NaOH solution (5.50 mL, 10.99 mmol) while maintaining the internal temperature at less than 5° C. The reaction was allowed to warm to room temperature and stirred for 1 hour. The white solid was filtered off and washed well with acetone to afford 5-bromo-4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (3.28 g, 99%) as a pale cream solid.

Aufarbeitung

  1. temperaturecooled to between −5° C. and 5° C
  2. temperaturewhile maintaining the internal temperature at less than 5° C
  3. stirringstirred for 1 hour
  4. filtrationThe white solid was filtered off
  5. washwashed well with acetone

Quellen und Nachweise

ORD-Eintrag
ord-45c9b267ca0e4defbb32d5116da05eb0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101623B2

Verknüpfte Notizen

Wird geladen…