5,6-Diamino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracil → 8-(2-Acetaminobenzyl)-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine

HRID 29874Notes

Reaction equation

HRID 29874 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12](O)=O)[C:2]([CH3:4])=[O:3].[NH2:15][C:16]1[C:17](=[O:38])[N:18]([CH2:35][CH2:36][CH3:37])[C:19](=[O:34])[N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)[C:21]=1[NH2:22]>>[NH:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]1[NH:15][C:16]2[C:17](=[O:38])[N:18]([CH2:35][CH2:36][CH3:37])[C:19](=[O:34])[N:20]([CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)[C:21]=2[N:22]=1)[C:2]([CH3:4])=[O:3]

Participants

3

Reactant 2

HCID 116096655,6-Diamino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracilHCID 146221782-(2-Acetamidophenyl)acetic acid

Product 1

HCID 184495338-(2-Acetaminobenzyl)-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthine

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-7bb019b068904f8393a969b80936877d
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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