Hydrazine hydrate (1:1) → 3-[2-(4-Aminophenyl)ethyl]-1-propyl-8-[(4-thiazolyl)methyl]xanthine

HRID 1270222Notes

Reaction equation

HRID 1270222 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[C:20]3[N:19]=[C:18]([CH2:21][C:22]4[N:23]=[CH:24][S:25][CH:26]=4)[NH:17][C:16]=3[C:15](=[O:27])[N:14]([CH2:28][CH2:29][CH3:30])[C:13]2=[O:31])=[CH:6][CH:5]=1)([O-])=O.O.NN.[H][H]>[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]2[C:20]3[N:19]=[C:18]([CH2:21][C:22]4[N:23]=[CH:24][S:25][CH:26]=4)[NH:17][C:16]=3[C:15](=[O:27])[N:14]([CH2:28][CH2:29][CH3:30])[C:13]2=[O:31])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 184495013-[2-(4-Nitrophenyl)ethyl]-1-propyl-8-[(4-thiazolyl)methyl]xanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 99789243-[2-(4-Aminophenyl)ethyl]-1-propyl-8-[(4-thiazolyl)methyl]xanthine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By the method of Example 2, 4-thiazolylacetic 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-[(4-thiazolyl)methyl]xanthine. By methods well known in the art, 3-[2-(4-nitrophenyl)ethyl]-1-propyl-8-[(4-thiazolyl)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-[(4-thiazolyl)methyl]xanthine.

Sources & evidence

ORD record
ord-3c2dec4c00974554a8f01d4926f79015
Source dataset
uspto-grants-2007_04
Patent number
US07202252B2

Reaction notes

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