Hydrazine hydrate (1:1) → HCID 66996050, compound

HRID 1296594Notes

Reaction equation

HRID 1296594 reaction equation
[CH3:1][CH2:2][NH:3][CH2:4][CH2:5][N:6]1[C:14]2[C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH3:18])[C:11](=[O:19])[N:10]([CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=3)[C:9]=2[N:8]=[C:7]1[CH2:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1.O.NN.[H][H]>[Pd]>[NH2:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][N:10]2[C:9]3[N:8]=[C:7]([CH2:31][C:32]4[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=4)[N:6]([CH2:5][CH2:4][NH:3][CH2:2][CH3:1])[C:14]=3[C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH3:18])[C:11]2=[O:19])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 86600323HCID 86600323, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66996050HCID 66996050, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

By the method of Example 2, 3-pyridylacetic 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-[(3-pyridyl)methyl]xanthine. By the method of Example 3, this substance is reacted with sodium carbonate, 1,2-dichloroethane and ethylamine to yield 4,7-(2-ethylamino)ethyl-3-[2-(4-nitrophenyl)ethyl]-1-propyl-8-[(3-pyridyl)methyl]xanthine. By the method of Example 4, 7-(2-ethylamino)ethyl-3-[2-(4-nitrophenyl)ethyl]-1-propyl-8-[(3-pyridyl)methyl]xanthine is reduced with hydrazine hydrate or hydrogen gas in the presence of a palladium catalyst to yield 3-[2-(4-aminophenyl)ethyl]-7-(2-ethylamino)ethyl-1-propyl-8-[(3-pyridyl)methyl]xanthine free base. The corresponding hydrochloride salt is then made on exposure to an excess of hydrogen chloride in solution.

Sources & evidence

ORD record
ord-7c791ab60b3b45499bbacef59e9a75be
Source dataset
uspto-grants-2007_07
Patent number
US07247639B2

Reaction notes

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