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

HRID 29865Notes

Reaction equation

HRID 29865 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH3:19])[C:11](=[O:20])[N:10]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=4)[C:9]=3[N:8]=2)=[CH:4][CH:3]=1.O.NN.[H][H]>[Pd]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][N:10]2[C:9]3[N:8]=[C:7]([CH2:6][C:5]4[CH:32]=[CH:33][C:2]([F:1])=[CH:3][CH:4]=4)[NH:15][C:14]=3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH3:19])[C:11]2=[O:20])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 184495398-(4-Fluorobenzyl)-3-[2-(4-nitrophenyl)ethyl]-1-propylxanthineHCID 178418361HCID 178418361, compound

Product 1

HCID 100708113-[2-(4-Aminophenyl)ethyl]-8-(4-fluorobenzyl)-1-propylxanthine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

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

Sources & evidence

ORD record
ord-cd61a40f05b04a29befb6fa3eba5b794
Source dataset
uspto-grants-2008_09
Patent number
US07423041B2

Reaction notes

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