Water → 6-Chloro-7-iodo-7-deazapurine

HRID 2207516Notes

Reaction equation

HRID 2207516 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.O>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

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 148092816-Chloro-7-iodo-7-deazapurineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (8.0 g, 52.32 mmol, 1.0 eq) in DMF (40 mL), NIS (15.7 g, 57.55 mmol, 1.1 eq) was added at 0° C. The reaction mixture was stirred overnight at room temperature. Water (40 mL) was added to the reaction mixture, extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under vacuum to give 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (14.6 g, 100% in yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-af1ec139cfdf487c99a27329f2d49b09
Source dataset
uspto-grants-2016_06
Patent number
US09376438B2

Reaction notes

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