Réaction #10530

Équation de réaction

3,4-dihydro-2H-pyran

2,6-Dichloro-9H-purine

4-toluenesulphonic acid monohydrate

sodium hydrogen carbonate

→

title compound

2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Solvants

water

ethyl acetate

ethyl acetate

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   AutreThe organic layer was separated
3. 3
   Lavagewashed sequentially with water and brine
4. 4
   Séchagedried over anhydrous magnesium sulphate
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent removed under reduced pressure
7. 7
   AutreThe residue was azeotroped with pentane (×2)

Mode opératoire

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 3,4-dihydro-2H-pyran (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 with pentane (×2) to afford the title compound as a slightly impure white solid (30.9 g).

Source