Water → 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine
Reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([Cl:11])[N:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.O.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[C:4]([Cl:11])[N:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2,6-Dichloro-9H-purine (20 g, 0.11 mol) and 4-toluenesulphonic acid monohydrate (0.2 g) were dissolved in ethyl acetate (300 ml), the mixture heated to 50° C. and a solution of 2,3-dihydropyran (12.6 ml, 0.14 mol) in ethyl acetate (50 ml) added slowly over 30 minutes. The reaction mixture was cooled to room temperature, water (100 ml) added and the pH of the solution adjusted to 7 by addition of a saturated aqueous solution of sodium hydrogen carbonate. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was azeotroped twice with pentane to afford the slightly impure title compound as a white solid (30.9 g).
Workup
- temperatureThe reaction mixture was cooled to room temperature
- customThe organic layer was separated
- washwashed sequentially with water and brine
- dry with materialdried over anhydrous magnesium sulphate
- filtrationfiltered
- customthe solvent removed under reduced pressure
- customThe residue was azeotroped twice with pentane
Sources & evidence
- ORD record
- ord-14ef5921a9db41bdbfa46c65aa0e855c
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06900309B1
Reaction notes
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