Hydrochloric Acid → 7-Benzylguanine Dihydrochloride
Reaction equation
C([C@]1(CO)O[C@@](C(=O)C)([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[C@](C(=O)C)(O)[C@]1(C(=O)C)O)(=O)C.[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[ClH:41]>C(#N)C>[ClH:41].[ClH:41].[CH2:33]([N:11]1[C:12]2[C:13](=[O:14])[NH:15][C:16]([NH2:17])=[N:18][C:19]=2[N:9]=[CH:10]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Tetraacetylguanosine (0.904 g, 2.00 mmols) was dissolved in 2 ml of acetonitrile, and 0.59 ml (2.48 equivalents) of benzyl bromide were added thereto. The reaction was conducted at 50° C. for 17 hours. After it was identified through HPLC that the starting material disappeared, 5 ml (29.6 equivalents) of conc. hydrochloric acid were added to the reaction solution, and the mixture was stirred at 50° C. for 3 hours. Then, the reaction solution turned black, and the gray solid was precipitated. The temperature was returned to room temperature, and 5 ml of methanol were added to the solid. The slurry was stirred for 20 minutes, and then filtered. The crystals were washed with 10 ml of methanol, and dried at 50° C. under reduced pressure to give 0.690 g of gray crystals in a yield of 57.4%.
Workup
- customthe gray solid was precipitated
- customwas returned to room temperature
- addition5 ml of methanol were added to the solid
- stirringThe slurry was stirred for 20 minutes
- filtrationfiltered
- washThe crystals were washed with 10 ml of methanol
- customdried at 50° C. under reduced pressure
Sources & evidence
- ORD record
- ord-e9d4a2f33b3440e092b488bb29a08643
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05942617
Reaction notes
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