Potassium Carbonate → HCID 18919031, compound

HRID 1291411Notes

Reaction equation

HRID 1291411 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].[C:13](=[O:16])([O-])[O-].[K+].[K+].[Cl:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1>CN(C=O)C.O>[Cl:19][C:20]1[CH:35]=[CH:34][C:23]([C:24]([C:26]2[CH:33]=[CH:32][C:29]([CH2:30][N:4]3[C:5](=[O:11])[C:6]4[N:7]([CH2:24][C:26]5[CH:33]=[CH:32][C:29]([C:13](=[O:16])[C:23]6[CH:22]=[CH:21][C:20]([Cl:19])=[CH:35][CH:34]=6)=[CH:28][CH:27]=5)[CH:8]=[N:9][C:10]=4[N:2]([CH3:1])[C:3]3=[O:12])=[CH:28][CH:27]=2)=[O:25])=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 706393-MethylxanthineHCID 98396514-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 18919031HCID 18919031, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methylxanthine (204 mg), potassium carbonate (340 mg) and 4-(4-chlorobenzoyl)benzyl bromide (754 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-hexane to provide the title compound as colorless solid (184 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-hexane

Sources & evidence

ORD record
ord-be4a89d4add14802ba0722ef5eb2fb89
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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