Hydrochloric Acid → 7-Benzylguanine Dihydrochloride
Reaction equation
[CH2:1]([Cl:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C@@]1(O)[C@@H](CO)O[C@@](C(=O)C)([N:19]2[C:29]3[N:28]=[C:26]([NH2:27])[NH:25][C:23](=[O:24])[C:22]=3[N:21]=[CH:20]2)[C@]1(C(=O)C)O)(=O)C.[ClH:38]>C(#N)C>[ClH:8].[ClH:38].[CH2:1]([N:21]1[C:22]2[C:23](=[O:24])[NH:25][C:26]([NH2:27])=[N:28][C:29]=2[N:19]=[CH:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Procedure
Benzyl chloride (2.14 ml, 10.0 equivalents) was added to 3.21 g of an acetonitrile solution containing 0.76 g (corresponding to 1.86 mmols) of triacetylguanosine obtained in Example 1, and the mixture was reacted at 70° C. for 71 hours. The temperature was returned to room temperature, and 3.13 ml (20 equivalents) of conc. hydrochloric acid were added thereto. When the mixture was reacted for 3 hours, the solid was precipitated. Ten milliliters of methanol were added thereto, and the slurry was stirred for 2 hours, and then filtered. The crystals were washed twice with 5 ml of methanol, and dried at 50° C. under reduced pressure for 2 hours to give 0.413 g of crystals in a yield of 70.9%.
Workup
- customthe mixture was reacted at 70° C. for 71 hours
- customwas returned to room temperature
- customWhen the mixture was reacted for 3 hours
- customthe solid was precipitated
- additionTen milliliters of methanol were added
- filtrationfiltered
- washThe crystals were washed twice with 5 ml of methanol
- customdried at 50° C. under reduced pressure for 2 hours
Sources & evidence
- ORD record
- ord-ee10c8d02acc48538d727dbc5df3aa6b
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05942617
Reaction notes
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