Butyl iodide → 7-[4-(4-Chlorobenzoyl)benzyl]-1-butyl-3-methylxanthine

HRID 1291413Notes

Reaction equation

HRID 1291413 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([C:18](=[O:26])[C:19]4[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=4)=[CH:14][CH:13]=3)[C:6]=2[C:5](=[O:27])[NH:4][C:3]1=[O:28].C(=O)([O-])[O-].[K+].[K+].[CH2:35](I)[CH2:36][CH2:37][CH3:38]>CN(C=O)C.O>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH2:11][N:7]3[C:6]4[C:5](=[O:27])[N:4]([CH2:35][CH2:36][CH2:37][CH3:38])[C:3](=[O:28])[N:2]([CH3:1])[C:10]=4[N:9]=[CH:8]3)=[CH:17][CH:16]=2)=[O:26])=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 189188013-Methyl-7-[4-(4-chlorobenzoyl)benzyl]xanthine

Product 1

HCID 189190507-[4-(4-Chlorobenzoyl)benzyl]-1-butyl-3-methylxanthineYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-7-[4-(4-chlorobenzoyl)-benzyl]xanthine (612 mg), potassium carbonate (228 mg) and butyl iodide (430 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 =1:1) and recrystallized from ethyl acetate to provide the title compound as colorless solid (147 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 =1:1)
  6. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-40956e029ef5486fb8162653b109f8bf
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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