1-Butanol → 2-chloro-N-[(3-iodophenyl)-methyl]-9-(tetrahydro-3-thienyl)-9H-purin-6-amine
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][S:13][CH2:12]2)=[C:4](Cl)[N:3]=1.C(O)CCC.[I:22][C:23]1[CH:24]=[C:25]([CH2:29][NH2:30])[CH:26]=[CH:27][CH:28]=1>C(O)(C)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:15][CH2:14][S:13][CH2:12]2)=[C:4]([NH:30][CH2:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([I:22])[CH:24]=2)[N:3]=1Participants
Procedure
The operation is carried out as in Stage 2 of Example 5 starting from 160 mg of the product obtained in Stage 1 of Example 5, 3 ml of butanol and using 0.114 ml of 3-iodo-benzenemethanamine in place of the benzylamine and the reaction medium is taken to a temperature of approximately 80 to 85° C. for approximately 30 hours, left to return to ambient temperature, diluted with 3 ml of isopropanol, placed for approximately one hour at a temperature of approximately 0° C., followed by separating, washing with 5 ml of isopropanol and drying under vacuum to a temperature of approximately 50° C. After purification on silica eluting with methylene chloride/ethyl acetate in a proportion 90/10, 173 mg of expected product is thus obtained in the form of white-yellow crystals.
Workup
- waitleft
- customto return to ambient temperature
- waitplaced for approximately one hour at a temperature of approximately 0° C.
- customby separating
- washwashing with 5 ml of isopropanol
- customdrying under vacuum to a temperature of approximately 50° C
- customAfter purification on silica eluting with methylene chloride/ethyl acetate in a proportion 90/10, 173 mg of expected product
- customis thus obtained in the form of white-yellow crystals
Sources & evidence
- ORD record
- ord-baffa38d22f94dcba6a66410f31593a2
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122669B1
Reaction notes
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