Theophylline → 7-[4-(4-Methylbenzoyl)benzyl]-1,3-dimethylxanthine

HRID 1291421Notes

Reaction equation

HRID 1291421 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>CN(C=O)C.O>[CH3:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([C:27]2[CH:28]=[CH:29][C:30]([CH2:31][N:9]3[C:10]4[C:11](=[O:12])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:13])[C:6]=4[N:7]=[CH:8]3)=[CH:33][CH:34]=2)=[O:26])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 108807584-(4-Toluoyl)benzyl bromide

Product 1

HCID 189191537-[4-(4-Methylbenzoyl)benzyl]-1,3-dimethylxanthineYield 45.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-dimethylxanthine (99 mg), potassium carbonate (135 mg), 4-(4-methylbenzoyl)benzyl bromide (201 mg) in DMF (10 ml) was stirred at 60° C. for 5 hours. This reaction mixture was poured in water and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:5) and recrystallized from ethyl acetate-isopropyl ether to provide the title compound as colorless solid (98 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (hexane: ethyl acetate =1:5)
  6. customrecrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-e4edcaa068964357a3fa09f747dabab6
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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