N-Iodosuccinimide → 6-Chloro-7-iodo-7-deazapurine

HRID 243311Notes

Reaction equation

HRID 243311 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C1C(=O)N([I:18])C(=O)C1>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:10]([I:18])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 148092816-Chloro-7-iodo-7-deazapurineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (3.0 g, 20 mmol) and NIS (4.9 g, 20.1 mmol) in DMF (100 mL) was stirred in darkness at room temperature overnight. Then the mixture was concentrated in vacuo. The residue was treated with 10% Na2SO3 and filtered to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (4.0 g, yield 72%) as a yellow solid.

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. additionThe residue was treated with 10% Na2SO3
  3. filtrationfiltered

Sources & evidence

ORD record
ord-73d6df0133f8487b9ca3c8eb415e2d25
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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