1H-Purine-2,6-dione, 3,7-dihydro-3-butyl-8-methyl-1-(2-propenyl)- → 1H-Purine-2,6-dione, 3,7-dihydro-3-butyl-8-methyl-1-propyl-

HRID 1380399Notes

Reaction equation

HRID 1380399 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH3:15])=[N:9][C:8]=2[N:7]([CH2:16][CH2:17][CH2:18][CH3:19])[C:5]1=[O:6])[CH:2]=[CH2:3]>C(O)C.[Pd]>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH3:15])=[N:9][C:8]=2[N:7]([CH2:16][CH2:17][CH2:18][CH3:19])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 30673101H-Purine-2,6-dione, 3,7-dihydro-3-butyl-8-methyl-1-(2-propenyl)-

Product 1

HCID 30673131H-Purine-2,6-dione, 3,7-dihydro-3-butyl-8-methyl-1-propyl-Yield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5 g of 1-allyl-3-butyl-8-methyl xanthine (Example 1) are dissolved in 100 ml of ethanol in a hydrogenation apparatus, followed by the addition of 500 mg of Pd (10%)/C. Hydrogenation is carried out at ambient temperature until the consumption of hydrogen is over (approximately 1 hour). The mixture is filtered under heat, the precipitate is washed with ethanol and the solvent is evaporated from the filtrate, leaving 5 g of colourless crystals which are recrystallised from methanol. Mp: 174°-175° C. C-NMR (Table 2).

Workup

  1. customHydrogenation is carried out at ambient temperature until the consumption of hydrogen
  2. customis over (approximately 1 hour)
  3. filtrationThe mixture is filtered
  4. temperatureunder heat
  5. washthe precipitate is washed with ethanol
  6. customthe solvent is evaporated from the filtrate

Sources & evidence

ORD record
ord-220c296f9b84406e84970d6ba18c1785
Source dataset
uspto-grants-1986_04
Patent number
US04581451

Reaction notes

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