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

HRID 419735Notes

Reaction equation

HRID 419735 reaction equation
[CH:1]1[C:5]2[C:6]([Cl:10])=[N:7][CH:8]=[N:9][C:4]=2[NH:3][CH:2]=1.[I:11]N1C(=O)CCC1=O>CN(C=O)C>[Cl:10][C:6]1[C:5]2[C:1]([I:11])=[CH:2][NH:3][C:4]=2[N:9]=[CH:8][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 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 6-chloro-7-deazapurine (10.75 g, 70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) in 400 mL of dry DMF and leave at ambient temperature in the darkness over night. Evaporate the solvent. Distribute the dark residue between 500 mL of ethyl acetate and 150 mL of 10% Na2SO3. Wash the organic fraction with 10% Na2SO3 (2×100 mL), saturate aqueous sodium chloride solution (150 mL), dry over Na2SO4 and evaporate. Crystallize the yellow residue from ethanol to yield 16.2 g (83%) of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine as off-white crystals. Evaporate the mother liquor, dissolve in toluene, and purify by flush chromatography on silica gel (7×4 cm). Wash the column with toluene until the eluant is colourless then elute the title compound with 5% ethyl acetate in toluene to give an additional 3.5 g of the product.

Workup

  1. customleave at ambient temperature in the darkness over night
  2. customEvaporate the solvent
  3. washWash the organic fraction with 10% Na2SO3 (2×100 mL)
  4. concentrationsaturate aqueous sodium chloride solution (150 mL)
  5. dry with materialdry over Na2SO4
  6. customevaporate
  7. customCrystallize the yellow residue from ethanol

Sources & evidence

ORD record
ord-d4377905823849599b652795f5d5e1b4
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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