(R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine → (R)-1-(5-Acetoxyhexyl)-8-aminomethyl-7-ethoxymethyl-3-methylxanthine

HRID 1835713Notes

Reaction equation

HRID 1835713 reaction equation
[C:1]([O:4][C@H:5]([CH3:28])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][O:22][CH2:23][CH3:24])[C:16]([C:25]#[N:26])=[N:15][C:14]=2[N:13]([CH3:27])[C:11]1=[O:12])(=[O:3])[CH3:2].[H][H]>[Pd].C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:28])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH2:21][O:22][CH2:23][CH3:24])[C:16]([CH2:25][NH2:26])=[N:15][C:14]=2[N:13]([CH3:27])[C:11]1=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 54159356(R)-1-(5-Acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 53959679(R)-1-(5-Acetoxyhexyl)-8-aminomethyl-7-ethoxymethyl-3-methylxanthineYield 105.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

A suspension of (R)-1-(5-acetoxyhexyl)-8-cyano-7-ethoxymethyl-3-methylxanthine (750 mg, 1.92 mmol) and 10% palladium on carbon (250 mg) in glacial acetic acid (40 ml) was treated with hydrogen gas (80 psi) on a Parr shaker for 3 hours. The mixture was filter through a pad of celite and then the filtrate was concentrated under reduced pressure to provide the acetic acid salt of (R)-1-(5-Acetoxyhexyl)-8-aminomethyl-7-ethoxymethyl-3-methylxanthine (800 mg, 91% yield) as a pale yellow oil.

Workup

  1. filtrationThe mixture was filter through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8894345278ee499abda4bf78f6bd0b9e
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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