5,6-Diamino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracil → HCID 178456519, compound

HRID 29872Notes

Reaction equation

HRID 29872 reaction equation
[NH:1]1[C:5]([CH2:6][C:7](O)=O)=[N:4][N:3]=[N:2]1.[NH2:10][C:11]1[C:12](=[O:33])[N:13]([CH2:30][CH2:31][CH3:32])[C:14](=[O:29])[N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:16]=1[NH2:17]>>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][N:15]2[C:16]3[N:17]=[C:7]([CH2:6][C:5]4[NH:1][N:2]=[N:3][N:4]=4)[NH:10][C:11]=3[C:12](=[O:33])[N:13]([CH2:30][CH2:31][CH3:32])[C:14]2=[O:29])=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

3

Reactant 2

HCID 116096655,6-Diamino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracilHCID 178525261HCID 178525261, compound

Product 1

HCID 178456519HCID 178456519, compound

Procedure

By the method of Example 2, 1H-tetrazole-5-acetic acid is reacted with 5,6-diamino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracil (6) to yield 3-[2-(4-nitrophenyl)ethyl]-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine. By methods well known in the art, 3-[2-(4-nitrophenyl)ethyl]-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine is reduced with hydrazine hydrate or hydrogen gas in the presence of a palladium catalyst to yield 3-[2-(4-aminophenyl)ethyl]-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine.

Sources & evidence

ORD record
ord-350bbc0ab9f54bd999fbb9d004038f88
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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