HCID 53813342, compound → HCID 53957188, compound

HRID 1814964Notes

Reaction equation

HRID 1814964 reaction equation
[OH:1][C@@H:2]([CH3:30])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]([CH2:25][N:26]=[N+]=[N-])=[N:12][C:11]=2[N:10]([CH3:29])[C:8]1=[O:9].[H][H]>C(O)C.[Pd]>[OH:1][C@@H:2]([CH3:30])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]([CH2:25][NH2:26])=[N:12][C:11]=2[N:10]([CH3:29])[C:8]1=[O:9]

Participants

5

Reactant 2

HCID 53813342HCID 53813342, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53957188HCID 53957188, compoundYield 251.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-1-(5-hydroxyhexyl)-7-benzyl-8-azidomethyl-3-methylxanthine (1.7 g, 1.65 mmol) in ethanol (100 ml) was added 10% palladium on carbon catalyst (0.6 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 (S)-1-(5-hydroxyhexyl)-7-benzyl-8-aminomethyl-3-methylxanthine (1.6 g, 100% yield).

Workup

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

Sources & evidence

ORD record
ord-cde600407c6845fb960674525e071016
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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