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

HRID 2099167Notes

Reaction equation

HRID 2099167 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.[I:11]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[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

Participants

4

Reactant 2

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

Product 1

HCID 148092816-Chloro-7-iodo-7-deazapurineYield 82.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (30 g/0.02 mol) dissolved in 80 mL of chloroform was added 4.5 grams (0.02 mol) of N-iodosuccinimide and the resulting mixture heated at reflux for 1 hour. After cooling to room temperature, the percipitate was removed by flitration and dried under reduced pressure affording 4.6 grams (82%) of the title compound.

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 1 hour
  3. customthe percipitate was removed by flitration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2b37e7f6295d4bb287d87f41a99e6a36
Source dataset
uspto-grants-2009_08
Patent number
US07569569B2

Reaction notes

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