Hydrochloric Acid → 2-Amino-7-benzyl-1H-purin-6(7H)-one
Reaction equation
[CH2:1](Br)[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.Cl>C(#N)C>[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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
Benzyl bromide (0.73 ml, 2.50 equivalents) was added to 4.24 g of an acetonitrile solution containing 1.0 g (corresponding to 2.45 mmols) of triacetylguanosine obtained in Example 1, and the mixture was stirred at 60° C. for 19 hours. The temperature was returned to room temperature, and 2.1 ml (10 equivalents) of conc. hydrochloric acid were added thereto. The mixture was reacted for 2 hours. The solid was precipitated in 1.5 hours. 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 55° C. under reduced pressure for 3 hours to give 0.61 g of 7-benzylguanine in a yield of 79.2%.
Workup
- customwas returned to room temperature
- customThe mixture was reacted for 2 hours
- customThe solid was precipitated in 1.5 hours
- additionTen milliliters of methanol were added
- stirringthe slurry was stirred for 2 hours
- filtrationfiltered
- washThe crystals were washed twice with 5 ml of methanol
- customdried at 55° C. under reduced pressure for 3 hours
Sources & evidence
- ORD record
- ord-df70002c8b614f838a3b45493125a722
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06252075B1
Reaction notes
Loading…