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

HRID 1865789Notes

Reaction equation

HRID 1865789 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>[CH:2]1[NH:3][C:4]2[N:9]=[CH:8][N:7]=[C:6]([Cl:10])[C:5]=2[C:1]=1[I:11]

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

6-Chloro-7-deazapurine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 ml of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The dark residue was distributed between 500 ml of ethyl acetate and 150 ml of 10% Na2SO3. Organic fraction was washed with 10% Na2SO3 (2×100 ml), brine (150 ml), dried over Na2SO4 and evaporated. The yellow residue was crystallized from ethanol to yield 16.2 g (83%) of the title compound as off white crystals. The mother liquid was evaporated, dissolved in toluene, and purified by flush chromatography on silica gel (7×4 cm). The column was washed with toluene until the eluent was colorless than the title compound was eluted with 5% ethyl acetate in toluene to give additional 3.5 g of the title product.

Workup

  1. waitleft at ambient temperature in the darkness over night
  2. customThe solvent was evaporated
  3. washOrganic fraction was washed with 10% Na2SO3 (2×100 ml), brine (150 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe yellow residue was crystallized from ethanol

Sources & evidence

ORD record
ord-0effbd62e52944f8a40be8c9eacde06f
Source dataset
uspto-grants-2009_12
Patent number
US07629328B2

Reaction notes

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