HCID 20773486, compound → HCID 20773485, compound

HRID 1814968Notes

Reaction equation

HRID 1814968 reaction equation
[N:1]([C@H:4]([CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[NH:16][C:15]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:14][C:13]=2[N:12]([CH3:29])[C:10]1=[O:11])=[N+]=[N-].[H][H]>C(O)C.[Pd]>[NH2:1][C@H:4]([CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:18](=[O:19])[C:17]2[NH:16][C:15]([CH2:20][NH:21][C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[N:14][C:13]=2[N:12]([CH3:29])[C:10]1=[O:11]

Participants

5

Reactant 2

HCID 20773486HCID 20773486, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20773485HCID 20773485, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (R)-1-(5-azidohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.7 g, 1.6 mmol) in ethanol (40 ml) was added 10% palladium on carbon catalyst (0.3 g). The mixture was treated with hydrogen gas (50 psi) on a Parr shaker for 18 hours. Removal of the catalyst by filtration and evaporation of the solvent under reduced pressure provided (R)-1-(5-aminohexyl)-8-(N-BOC-aminomethyl)-3-methylxanthine (0.5 g, 77% yield) as a white solid.

Workup

  1. customRemoval of the catalyst
  2. filtrationby filtration and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-85a6d7541e81400eb095b098c5f253e1
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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