Reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:25]([NH:26][CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[N:24][C:23]3[C:18]2=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:12][CH:11]=1>C(O)CCC>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:25]([NH:26][CH:27]3[CH2:28][CH2:29][N:30]([CH2:2][CH2:1][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=4)[CH2:31][CH2:32]3)=[N:24][C:23]3[C:18]2=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:12][CH:11]=1Participants
4
Procedure
A mixture of 1.93 parts of 2-ethenylpyridine, 5 parts of 9-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-9H-purin-8-amine and 80 parts of 1-butanol was stirred and refluxed overnight. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using first a mixture of trichloromethane and methanol (95:5 by volume) and then a mixture of trichloromethane and methanol, saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 1 part (15%) of 9-[(4-fluorophenyl)methyl]-N-[1-[2-(2-pyridinyl)ethyl]-4-piperidinyl]-9H-purin-8-amine; mp. 172.3° C. (compound 141).
Workup
- temperaturerefluxed overnight
- customThe reaction mixture was evaporated
- customThe residue was purified by column chromatography over silica gel using first
- additiona mixture of trichloromethane and methanol (95:5 by volume)
- additiona mixture of trichloromethane and methanol
- customThe pure fractions were collected
- customthe eluent was evaporated
- customThe residue was crystallized from acetonitrile
Sources & evidence
- ORD record
- ord-ccdd89b5515d4a498840c794f604ab87
- Source dataset
- uspto-grants-1993_11
- Patent number
- US05258380
Linked notes
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