(R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine → (R)-1-(5-acetoxyhexyl)-8-aminomethyl-7-benzyl-3-methylxanthine

HRID 1296406Notes

Reaction equation

HRID 1296406 reaction equation
[C:1]([O:4][C@H:5]([CH3:31])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([C:28]#[N:29])=[N:15][C:14]=2[N:13]([CH3:30])[C:11]1=[O:12])(=[O:3])[CH3:2].[H][H]>[Pd].C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:31])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([CH2:28][NH2:29])=[N:15][C:14]=2[N:13]([CH3:30])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 53812008(R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 54253673(R)-1-(5-acetoxyhexyl)-8-aminomethyl-7-benzyl-3-methylxanthine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of (R)-1-(5-acetoxyhexyl)-7-benzyl-8-cyano-3-methylxanthine (850 mg, 2.0 mmol) and 10% palladium on carbon (300 mg) in glacial acetic acid (60 ml) was treated with hydrogen gas (80 psi) on a Parr shaker for 3 hours. After filtering through a pad of celite, the filtrate was concentrated under reduced pressure to provide the acetic acid salt of (R)-1-(5-acetoxyhexyl)-8-aminomethyl-7-benzyl-3-methylxanthine.

Workup

  1. filtrationAfter filtering through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc115ce7f43b4a04ab19084a5a2dc1e0
Source dataset
uspto-grants-2007_07
Patent number
US07247630B2

Reaction notes

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