2-chloro-N-phenyl-9-(tetrahydro-3-thienyl)-9H-purin-6-amine → N2-(4-aminocyclo-hexyl)-N6-phenyl-9-(tetrahydro-3-thienyl)-9H-purin-2,6-diamine Dihydrochloride
Reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH2:8])[CH2:4][CH2:3]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH:19]2[CH2:23][CH2:22][S:21][CH2:20]2)=[C:12]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:11]=1>>[ClH:9].[ClH:9].[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:10]2[N:18]=[C:17]3[C:13]([N:14]=[CH:15][N:16]3[CH:19]3[CH2:23][CH2:22][S:21][CH2:20]3)=[C:12]([NH:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:11]=2)[CH2:4][CH2:3]1Participants
3
Procedure
The operation is carried out as in Stage 3 of Example 5 starting from 536 mg of trans-1,4-diaminocyclohexane and 156 mg of the product obtained in Stage 1 above, the reaction medium is taken to a temperature of approximately 140 to 145° C. for approximately 4 hours 30 minutes then left to return to ambient temperature. After purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 salification is carried out with 1.4 N hydrochloric acid in ethanol, followed by separating, washing and drying at a temperature of approximately 50° C. In this way 145 mg of expected product is obtained in the form of pink beige crystals.
Workup
- waitthen left
- customto return to ambient temperature
- customAfter purification on silica eluting with methanol/ammonium hydroxide (NH4OH) in a proportion of 98/2 salification
- customby separating
- washwashing
- customdrying at a temperature of approximately 50° C
Sources & evidence
- ORD record
- ord-faf43d0500834664ad5fac4604d546e1
- Source dataset
- uspto-grants-2007_04
- Patent number
- US07208598B2
Reaction notes
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