Ammonia → 7-(4-Diethylphosphonobutyl)-3-methylxanthine

HRID 1991Notes

Reaction equation

HRID 1991 reaction equation
C([N:8]1[C:17](=[O:18])[C:16]2[N:15]([CH2:19][CH2:20][CH2:21][CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[CH:14]=[N:13][C:12]=2[N:11]([CH3:31])[C:9]1=[O:10])C1C=CC=CC=1.N>C(O)C.[Pd]>[CH3:31][N:11]1[C:12]2[N:13]=[CH:14][N:15]([CH2:19][CH2:20][CH2:21][CH2:22][P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[C:16]=2[C:17](=[O:18])[NH:8][C:9]1=[O:10]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 22446290Diethyl [4-(1-benzyl-3-methylxanthin-7-yl)butyl]phosphonate

Product 1

HCID 153824337-(4-Diethylphosphonobutyl)-3-methylxanthine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

13 g (0.03 mol) of diethyl [4-(1-benzyl-3-methylxanthin-7-yl)-butyl]phosphonate were suspended in 150 ml of ethanol with 2 g of palladium on activated carbon (10%) and, after addition of 3 ml of concentrated ammonia solution, hydrogenated with shaking at 1.5 bar in the course of 48 hours. The catalyst was filtered off, the solvent was evaporated under reduced pressure and the residue which remained was crystallized from diisopropyl ether.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue which remained was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7770e21bea004978a0779f7b92547672
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Reaction notes

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