3-Pyridineacetic acid → 3-[2-(4-Nitrophenyl)ethyl]-1-propyl-8-[(3-pyridyl)methyl]xanthine
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](O)=O)[CH:2]=1.[NH2:11][C:12]1[C:13](=[O:34])[N:14]([CH2:31][CH2:32][CH3:33])[C:15](=[O:30])[N:16]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[C:17]=1[NH2:18]>>[N+:27]([C:24]1[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][N:16]2[C:17]3[N:18]=[C:8]([CH2:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)[NH:11][C:12]=3[C:13](=[O:34])[N:14]([CH2:31][CH2:32][CH3:33])[C:15]2=[O:30])=[CH:22][CH:23]=1)([O-:29])=[O:28]Participants
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-3f8054105f354760b3b5683668f8e6a8
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07247639B2
Reaction notes
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