Water → 4-chloro-5-iodo-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 243312Notes

Reaction equation

HRID 243312 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:12]1([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]=[C:19]2[CH:27](N)C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH2:27][C:19]3[N:18]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[N:20]=3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 434704871-(1-Phenyl-1H-benzoimidazol-2-yl)ethylamine

Product 1

HCID 866688814-chloro-5-iodo-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidineYield 85.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.15 g, 4.1 mmol), 1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine from Example 4 (1.0 g, 4.1 mol) 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 CH2Cl2 (20 mL×3). The combined organic layers were concentrated in vacuo to give 4-chloro-5-iodo-7-(1-phenyl-1H-benzoimidazol-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine (1.7 g, yield 85%) as brown solid.

Workup

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

Sources & evidence

ORD record
ord-46a28458793b489e95ace4618ed09efc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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