Potassium Iodide → 8-Chloro-7-(2-iodobenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 984815Notes

Reaction equation

HRID 984815 reaction equation
[Cl:1][C:2]1[NH:11][C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1.[I:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C.CCOC(C)=O.O>[Cl:1][C:2]1[N:11]([CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=2[I:15])[C:10]2[C:9](=[O:12])[N:7]([CH3:8])[C:6](=[O:13])[N:5]([CH3:14])[C:4]=2[N:3]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 106618-ChlorotheophyllineHCID 11430Potassium CarbonateHCID 1010641-(Chloromethyl)-2-iodobenzene

Product 1

HCID 225086268-Chloro-7-(2-iodobenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Chlorotheophylline (8.5 g, 39.6 mmol) was dissolved in 400 ml of DMF and 2-iodobenzyl chloride (10.0 g, 39.6 mmol), potassium carbonate (5.47 g, 39.6 mmol), and potassium iodide (10 mg, 0.06 mmol) were added. The mixture was stirred at room temperature for 7 days. Water (2500 ml) and EtOAc (800 ml) were added and the layers were separated. The aqueous layer was extracted with 2×500 ml of EtOAc, and the combined organic layer was washed with 500 ml of water, 500 ml of brine, dried over sodium sulphate, and filtered. The solvent was evaporated and the crude product was crystallized from diethyl ether and petrol, to give compound (5A) as white crystals. The mother liquor was evaporated and resuspended in diethyl ether and petrol, to give a second crop of compound (5A).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 2×500 ml of EtOAc
  3. washthe combined organic layer was washed with 500 ml of water, 500 ml of brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. customthe crude product was crystallized from diethyl ether and petrol

Sources & evidence

ORD record
ord-0554b8ada92042d794c0106cc4369542
Source dataset
uspto-grants-2005_03
Patent number
US06869947B2

Reaction notes

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