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

HRID 82156Notes

Reaction equation

HRID 82156 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[CH:18]=[CH:17][NH:16][C:14]=2[N:15]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(#N)C>[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[C:18]([I:1])=[CH:17][NH:16][C:14]=2[N:15]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 656671Sodium PyrosulfiteHCID 57067742-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 529112452-chloro-5-iodo-7H-pyrrolo(2,3-d)pyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Iodosuccinimide (742 g, 3.30 mol) was added to 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (482.5 g, 3.14 mol) in acetonitrile (2500 mL) at 12° C. The mixture was stirred at room temperature for 1 hour then sodium metabisulphite (650 g in 4500 mL of water) was added. The mixture was stirred for 1 hour then filtered to afford the title compound as a orange solid in 82% yield, 716.2 g.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. filtrationthen filtered

Sources & evidence

ORD record
ord-3d72ddf0a4204e41a42a87d18da72d71
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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