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Water → 4-chloro-1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-1H-Pyrazolo[3,4-d]pyrimidin-6-ylamine

HRID 243330
Notes
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Reaction equation

HRID 243330 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12.Cl[CH2:13][C:14]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[N:15]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[N:9]([CH2:13][C:14]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]=3)[N:10]=[CH:11][C:3]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amineHCID 202518962-(Chloromethyl)-1-phenyl-1H-benzimidazole

Product 1

HCID 866688834-chloro-1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-1H-Pyrazolo[3,4-d]pyrimidin-6-ylamineYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (1.0 g, 5.9 mmol), 2-(chloromethyl)-1-phenyl-1H-benzo[d]imidazole (1.4 g, 5.9 mmol) and K2CO3 (0.86 g, 6.2 mmol) in DMSO (20 mL) was stirred at room temperature overnight. Then the mixture was added H2O (50 mL) and extracted with CH2Cl2 (20 mL×3). The combined organic layers were concentrated in vacuo to give 4-chloro-1-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-1H-Pyrazolo[3,4-d]pyrimidin-6-ylamine (1.5 g, yield 68%) as orange solid.

Workup

  1. extractionextracted with CH2Cl2 (20 mL×3)
  2. concentrationThe combined organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-93ebebb7084a4f22979144aa08c70a53
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08653089B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes