Hydrochloric Acid → 2-Amino-7-benzyl-1H-purin-6(7H)-one
Reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[N:6]=[CH:7][N:8]([C@H]3[C@@H](O)[C@@H](O)[C@H](CO)O3)[C:9]=2[N:10]=1.Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>CS(C)=O>[NH2:1][C:2]1[NH:3][C:4](=[O:20])[C:5]2[N:6]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:7]=[N:8][C:9]=2[N:10]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 2-amino-9-((2R,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one (14 g, 49.47 mmol) in DMSO (50 mL) was added (bromomethyl)benzene (10 g, 59.36 mmol). The mixture was stirred at 50° C. overnight. Then the mixture was cooled to room temperature and HCl (50 mL, 10% w.w) was added and the mixture was stirred at 70° C. for 2 h. The reaction was cooled to room temperature, filtered and the filter cake was washed with water and ethanol and dried under vacuum to give 2-amino-7-benzyl-1H-purin-6(7H)-one (10 g, 74.2% yield) as grey solid. LCMS retention time 0.529 min; LCMS MH+ 242.
Workup
- temperatureThen the mixture was cooled to room temperature
- stirringthe mixture was stirred at 70° C. for 2 h
- temperatureThe reaction was cooled to room temperature
- filtrationfiltered
- washthe filter cake was washed with water and ethanol
- customdried under vacuum
Sources & evidence
- ORD record
- ord-ca1cfa1e94bf438f8d21e35bcab9c0a0
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359359B2
Reaction notes
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