Potassium Carbonate → 7-[4-(4-Chlorobenzoyl)benzyl]-1-ethyl-3-methylxanthine

HRID 1291327

Reaction equation

HRID 1291327 reaction equation
[CH2:1]([N:3]1[C:12](=[O:13])[C:11]2[NH:10][CH:9]=[N:8][C:7]=2[N:6]([CH3:14])[C:4]1=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=2)=[O:27])=[CH:24][CH:23]=1>CN(C=O)C.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][N:10]3[C:11]4[C:12](=[O:13])[N:3]([CH2:1][CH3:2])[C:4](=[O:5])[N:6]([CH3:14])[C:7]=4[N:8]=[CH:9]3)=[CH:30][CH:29]=2)=[O:27])=[CH:36][CH:37]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 129053881-Ethyl-3-methyl-3,7-dihydro-purine-2,6-dione

Product 1

HCID 189190887-[4-(4-Chlorobenzoyl)benzyl]-1-ethyl-3-methylxanthineYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In DMF (10 ml) was dissolved 1-ethyl-3-methylxanthine (385 mg), a production process for which is described in Journal of American Chemical Society 75, 114, 1953. To this solution were added potassium carbonate (415 mg) and 4-(4-chlorobenzoyl)benzyl bromide (619 mg) and the mixture was stirred at room temperature for 14 hours. This reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:4) and recrystallized (ethyl acetate-ether-hexane) to provide the title compound as white powder (207 mg, 25%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate=1:4)
  6. customrecrystallized (ethyl acetate-ether-hexane)

Sources & evidence

ORD record
ord-1c024184535542a8a97f6c3e6058ed6d
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Linked notes

Loading…