Potassium Carbonate → HCID 13747691, compound

HRID 1762547Notes

Reaction equation

HRID 1762547 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12](=[O:14])[CH3:13])[C:6]=2[C:5](=[O:15])[NH:4][C:3]1=[O:16].Cl[CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12](=[O:14])[CH3:13])[C:6]=2[C:5](=[O:15])[N:4]([CH2:18][CH2:19][CH2:20][CH2:21][C:22](=[O:24])[CH3:23])[C:3]1=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 824686-Chlorohexan-2-oneHCID 13747686HCID 13747686, compound

Product 1

HCID 13747691HCID 13747691, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22.2 g (0.1 mol) of 3-methyl-7-(2-oxopropyl)-xanthine from Example 7a are stirred together with 14.8 g (0.11 mol) of 1-chloro-5-hexanone and 15.2 g (0.11 mol) of potassium carbonate in 500 ml of dimethylformamide at 110° C. for 1.5 hours. The mixture is then allowed to cool slowly, with further stirring, and filtered, the salt on the suction filter is rinsed thoroughly with dimethylformamide, the solution is concentrated under reduced pressure, the residue is taken up in 200 ml of methanol, 50 ml of water and 2 ml of concentrated sulfuric acid are added and the mixture is boiled under reflux for one hour. After removal of the methanol in vacuo, the residue is rendered alkaline with 33% strength sodium hydroxide solution and the mixture is extracted thoroughly by shaking with chloroform. The combined chloroform extracts are washed with a little water until neutral and dried over sodium sulfate and the solvent is distilled off in vacuo, whereupon 25.8 g of solid crude product (80.5% of theory) are obtained and are recrystallized from ethanol, with the addition of petroleum ether, at the boiling point.

Workup

  1. temperatureto cool slowly, with further stirring
  2. filtrationfiltered
  3. filtrationthe salt on the suction filter
  4. washis rinsed thoroughly with dimethylformamide
  5. concentrationthe solution is concentrated under reduced pressure
  6. addition50 ml of water and 2 ml of concentrated sulfuric acid are added
  7. temperatureunder reflux for one hour
  8. customAfter removal of the methanol in vacuo
  9. extractionthe mixture is extracted thoroughly
  10. washThe combined chloroform extracts are washed with a little water until neutral and
  11. dry with materialdried over sodium sulfate
  12. distillationthe solvent is distilled off in vacuo, whereupon 25.8 g of solid crude product (80.5% of theory)
  13. customare obtained
  14. customare recrystallized from ethanol, with the addition of petroleum ether, at the boiling point

Sources & evidence

ORD record
ord-82177f0fabf9413aae217ce15d897c96
Source dataset
uspto-grants-1989_05
Patent number
US04833146

Reaction notes

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