3-Butyl-1-(prop-2-en-1-yl)-3,9-dihydro-1H-purine-2,6-dione → Xanthine

HRID 1742203Notes

Reaction equation

HRID 1742203 reaction equation
C([N:4]1[C:13](=[O:14])[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[N:7](CCCC)[C:5]1=[O:6])C=C.[BH4-].[Na+]>O.C1COCC1.[OH-].[Na+].C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[NH:4]1[C:13](=[O:14])[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[NH:7][C:5]1=[O:6]

Participants

7

Reactant 2

HCID 30673113-Butyl-1-(prop-2-en-1-yl)-3,9-dihydro-1H-purine-2,6-dioneHCID 4311764Sodium borohydride

Product 1

HCID 1188Xanthine

Reagents, catalysts & solvents 4

HCID 15337Mercuric acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

16 g (0.050 mole) of mercury (II) acetate are dissolved in 250 ml water. 12.4 g (0.05 mole) of 1-allyl-3-butyl xanthine (prepared as described above from 1-butyl-5-formylamino-6-aminouracil and allyl bromide) dissolved in 250 ml of THF are added dropwise with stirring over a period of 10 minutes. After a few minutes, a precipitate is formed. Stirring is continued for 30 minutes, after which the mixture is cooled in an ice bath. 68 ml of 3 N NaOH are added, followed by the dropwise addition of 60 ml of a freshly prepared 0.5 M solution of NaBH4 in 3 N NaOH. On completion of the addition, stirring is continued for another 15 minutes. The solution is neutralized to pH 4-5 with 6 N HC1 (approximately 60 ml), saturated with NaC1 and the xanthine extracted with dichloromethane (3×200 ml). The organic extract is dried and the solvent is evaporated: 12.9 g of crude product containing 20% of starting product. The products are separated by passing the mixture through a column of silica using chloroform as eluent for the starting product and chloroform/methanol (95/5) for the hydroxylated xanthine (9.5 g) . The xanthine is recrystallized twice from water: 8.5 g (64%); Mp. 157-158° C.

Workup

  1. additionare added dropwise
  2. waitAfter a few minutes
  3. customa precipitate is formed
  4. stirringStirring
  5. waitis continued for 30 minutes
  6. temperatureafter which the mixture is cooled in an ice bath
  7. additionOn completion of the addition
  8. stirringstirring
  9. waitis continued for another 15 minutes
  10. extractionthe xanthine extracted with dichloromethane (3×200 ml)
  11. extractionThe organic extract
  12. customis dried
  13. customthe solvent is evaporated
  14. addition12.9 g of crude product containing 20% of starting product
  15. customThe products are separated
  16. customThe xanthine is recrystallized twice from water

Sources & evidence

ORD record
ord-a628c438e2894086bad702e59d2cc9a5
Source dataset
uspto-grants-1994_08
Patent number
US05338741

Reaction notes

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