Hydrazine hydrate (1:1) → 3-[2-(4-Aminophenyl)ethyl]-8-benzyl-1-(3-methoxypropyl)xanthine

HRID 29878Notes

Reaction equation

HRID 29878 reaction equation
COCCCN=C=O.[CH2:9]([C:16]1[NH:24][C:23]2[C:22](=[O:25])[N:21]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:20](=[O:31])[N:19]([CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([N+:40]([O-])=O)=[CH:36][CH:35]=3)[C:18]=2[N:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O.NN.[H][H]>[Pd]>[NH2:40][C:37]1[CH:36]=[CH:35][C:34]([CH2:33][CH2:32][N:19]2[C:18]3[N:17]=[C:16]([CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[NH:24][C:23]=3[C:22](=[O:25])[N:21]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:20]2=[O:31])=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 18449563HCID 18449563, compoundHCID 189419151-Isocyanato-3-methoxypropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 184494173-[2-(4-Aminophenyl)ethyl]-8-benzyl-1-(3-methoxypropyl)xanthine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By methods well known in the art 3-methoxypropyl isocyanate is converted into 8-benzyl-3-[2-(4-nitrophenyl)ethyl]-1-(3-methoxypropyl)xanthine, which in turn, is reduced with hydrazine hydrate or hydrogen gas in the presence of a palladium catalyst to yield 3-[2-(4-aminophenyl)ethyl]-8-benzyl-1-(3-methoxypropyl)xanthine.

Sources & evidence

ORD record
ord-dc63ade88f694b8e9b31757ae904140a
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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