Adenine → HCID 178471844, compound
Reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>>[NH2:10][CH:9]1[NH:1][CH:2]=[N:3][C:4]2[N:5]([CH2:13][CH2:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[N:7][C:8]1=2Participants
Procedure
Adenine (10.00 g., 74.00 mmol) was placed into a clean, dry 500 ml round bottom flask equipped with a magnetic stirring bar, reflux condenser, and a CaCl2 drying tube. Absolute ethanol (360 ml) was added and the solution was stirred. To the suspension was added a small piece of Sodium (approximately 75 mg). When the Sodium had completely reacted, 22.2 g (0.222 mol) ethyl acrylate was added to the suspension and the mixture was brought to reflux. Reflux was continued overnight for approximately 18 hours and the resulting lime colored homogeneous solution was allowed to cool slowly to room temperature. Crystals were allowed to form at 4° C. The solution was filtered by Buchner vacuum filtration and the solid was washed with anhydrous ether. Upon drying, 15.2 g (64.6 mmol) of 3-(1,6-dihydro-6-amino-9H-purin-9-yl)propionic acid, ethyl ester (AIT-0026) was obtained. Yield: 87%.
Workup
- customdry 500 ml round bottom flask
- customequipped with a magnetic stirring bar
- temperaturereflux condenser, and a CaCl2 drying tube
- additionAbsolute ethanol (360 ml) was added
- additionTo the suspension was added a small piece of Sodium (approximately 75 mg)
- customWhen the Sodium had completely reacted
- temperatureto reflux
- temperatureReflux
- customto form at 4° C
- filtrationThe solution was filtered by Buchner vacuum filtration
- washthe solid was washed with anhydrous ether
- customUpon drying
Sources & evidence
- ORD record
- ord-af345adb25054393a88791f3e4c4d79e
- Source dataset
- uspto-grants-1992_02
- Patent number
- US05091432
Reaction notes
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