N-Iodosuccinimide → 2,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidine

HRID 645701Notes

Reaction equation

HRID 645701 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[I:12]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([Cl:11])[C:5]2[C:10]([I:12])=[CH:9][NH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 574159022,4-Dichloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidineYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (2.0 g, 10.6 mmol) in CH2Cl2 (32 mL) was added N-iodosuccinimide (NIS) (2.4 g, 10.6 mmol) at room temperature. After stirring for 1 h, the resulting precipitates were collected by filtration to give 2,4-dichloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (1.8 g).

Workup

  1. customthe resulting precipitates
  2. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3f571cc5feeb4a77a21c02cd393de657
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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