Water → 4-chloro-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 243309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243309
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.Cl[CH2:12][C:13]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]2[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=2[N:14]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([CH2:12][C:13]3[N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:16]4[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=4[N:14]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-HCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazole

Produkt 1

HCID 866688804-chloro-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidineAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.62 g, 4.1 mmol), 2-(chloromethyl)-1-phenyl-1H-benzo[d]imidazole (1.0 g, 4.1 mmol) and K2CO3 (0.6 g, 4.3 mmol) in DMSO (20 mL) was stirred at room temperature overnight. Then the mixture was added H2O (50 mL) and extracted with EtOAc (20 mL×3). The combine organic layers were concentrated in vacuo to give 4-chloro-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine (1.2 g, yield 80%) as brown solid.

Aufarbeitung

  1. extractionextracted with EtOAc (20 mL×3)
  2. concentrationThe combine organic layers were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-854c2282f44b47f9a91370f1aa5ccd1c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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