HCID 9923492, compound → HCID 10359295, compound

HRID 1939234Notes

Reaction equation

HRID 1939234 reaction equation
[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH:15]3[CH2:20][CH:19]4[CH2:21][CH:16]3[CH:17]=[CH:18]4)=[N:9][C:8]=2[N:7]([CH2:22][CH2:23][CH3:24])[C:5]1=[O:6])[CH2:2][CH3:3].[H][H]>C(O)C.[Pd]>[CH2:1]([N:4]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH:15]3[CH2:20][CH:19]4[CH2:21][CH:16]3[CH2:17][CH2:18]4)=[N:9][C:8]=2[N:7]([CH2:22][CH2:23][CH3:24])[C:5]1=[O:6])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 9923492HCID 9923492, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10359295HCID 10359295, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.0 g (3.1 mmol) of 1,3-dipropyl-8-(5-norbornen-2-yl)xanthine are hydrogenated under pressure in 30 ml of ethanol, with the addition of palladium/charcoal, until no further uptake of hydrogen can be detected. The catalyst is filtered off, the filtrate is concentrated by evaporation and the residue is chromatographed on silica gel (Ch2Cl2 /CH3OH 99:1). 0.4 g of the title compound are obtained in the form of white crystals (39% of theory), m.p. 136°-138° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated by evaporation
  3. customthe residue is chromatographed on silica gel (Ch2Cl2 /CH3OH 99:1)

Sources & evidence

ORD record
ord-91f5aac9b4d94e03bbc74e92c56fd78c
Source dataset
uspto-grants-1997_12
Patent number
US05696124

Reaction notes

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