2-Chloroadenosine → 2-[6-Amino-2-(indan-2-ylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol
Reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH:22]1[NH2:30].C(N(C(C)C)CC)(C)C.C(O)CC(C)C>C(OCC)(=O)C>[CH2:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH:22]1[NH:30][C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11]Participants
6
Procedure
A mixture of 1.0 g of 2-chloroadenosine, 1.2 g of 2-indanylamine, and 1.6 ml of diisopropylethylamine and 1.0 ml of isoamyl alcohol is refluxed for 16 hours. The reaction mixture is diluted with ethyl acetate and washed with saturated sodium bicarbonate solution. After drying over magnesium sulfate the solvent is removed in vacuo and the residue is chromatographed on silica gel with 10:1 methylene chloride/ammonia saturated methanol as the eluent. The resulting product is recrystallized from methanol to afford 2-(2-indanylamino)-adenosine melting at 129°-132°.
Workup
- temperatureis refluxed for 16 hours
- washwashed with saturated sodium bicarbonate solution
- dry with materialAfter drying over magnesium sulfate the solvent
- customis removed in vacuo
- customthe residue is chromatographed on silica gel with 10:1 methylene chloride/ammonia saturated methanol as the eluent
- customThe resulting product is recrystallized from methanol
Sources & evidence
- ORD record
- ord-82de9719748d4c5bb7e8257c39e9438c
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05034381
Reaction notes
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