Potassium Carbonate → HCID 13298147, compound

HRID 1706370Notes

Reaction equation

HRID 1706370 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][CH2:12][CH3:13])[C:6]=2[C:5](=[O:14])[NH:4][C:3]1=[O:15].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH:25]=[CH2:26]>CN(C)C=O>[CH2:26]([N:4]1[C:5](=[O:14])[C:6]2[N:7]([CH2:11][CH2:12][CH3:13])[CH:8]=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:15])[CH2:25][CH:24]=[CH2:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 33143973-Methyl-7-propylpurine-2,6-dione

Product 1

HCID 13298147HCID 13298147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

20.8 g of 3-methyl-7-propyl-xanthine, 13.8 g of anhydrous potassium carbonate and 13.5 g of 4-bromo-but-1-ene are refluxed for 8 hours in 150 ml of dimethylformamide, and the solvent is then removed under reduced pressure. The residue is then dissolved in 150 ml of 1 N sodium hydroxide solution and the alkaline solution is extracted with methylene chloride. The residue obtained after evaporation of the methylene chloride is triturated with 100 ml of diisopropyl ether and unreacted 3-methyl-7-propyl-xanthine is removed. 15.6 g (70% of theory relative to 3-methyl-7-propyl-xanthine consumed) of the title compound of melting point 48° C. (from n-hexane) are obtained from the filtrate.

Workup

  1. customthe solvent is then removed under reduced pressure
  2. dissolutionThe residue is then dissolved in 150 ml of 1 N sodium hydroxide solution
  3. extractionthe alkaline solution is extracted with methylene chloride
  4. customThe residue obtained
  5. customafter evaporation of the methylene chloride
  6. customis triturated with 100 ml of diisopropyl ether and unreacted 3-methyl-7-propyl-xanthine
  7. customis removed
  8. custom15.6 g (70% of theory relative to 3-methyl-7-propyl-xanthine consumed) of the title compound of melting point 48° C. (from n-hexane)
  9. customare obtained from the filtrate

Sources & evidence

ORD record
ord-54a78eda6957459e89996d2f292d617b
Source dataset
uspto-grants-1980_06
Patent number
US04207321

Reaction notes

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