Hydrazine hydrate (1:1) → 8-(2-Acetaminobenzyl)-3-[2-(4-aminophenyl)ethyl]-1-propylxanthine

HRID 29875Notes

Reaction equation

HRID 29875 reaction equation
[NH:1]([C:5]1[CH:36]=[CH:35][CH:34]=[CH:33][C:6]=1[CH2:7][C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)[C:10]=2[N:9]=1)[C:2]([CH3:4])=[O:3].O.NN.[H][H]>[Pd]>[NH:1]([C:5]1[CH:36]=[CH:35][CH:34]=[CH:33][C:6]=1[CH2:7][C:8]1[NH:16][C:15]2[C:14](=[O:17])[N:13]([CH2:18][CH2:19][CH3:20])[C:12](=[O:21])[N:11]([CH2:22][CH2:23][C:24]3[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=3)[C:10]=2[N:9]=1)[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 184495338-(2-Acetaminobenzyl)-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 117539978-(2-Acetaminobenzyl)-3-[2-(4-aminophenyl)ethyl]-1-propylxanthine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By the method of Example 2, 2-(acetamino)phenylacetic acid is reacted with 5,6-diamino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracil (6) to yield 8-(2-acetaminobenzyl)-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine. By methods well known in the art, 8-(2-acetaminobenzyl)-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine is reduced with hydrazine hydrate or hydrogen gas in the presence of a palladium catalyst to yield 8-(2-acetaminobenzyl)-3-[2-(4-aminophenyl)ethyl]-1-propylxanthine.

Sources & evidence

ORD record
ord-255f1ef04b3849e3a872faa66fdb4e4f
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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