3,4-dihydro-2H-pyran → 2,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Participants

Reaction Conditions

Reaction Steps

2,6-Dichloro-9H-purine (20 g, 0.11 mol) and 4-toluenesulphonic acid monohydrate (0.2 g) were dissolved in stirred ethyl acetate (300 ml), the mixture heated to 50° C. and a solution of 2,3dihydropyran (12.6 ml, 0.14 mol) in ethyl acetate (50 ml) added slowly over 30 min. The reaction mixture was then cooled to room temperature and water (100 ml) added and the pH of the solution adJusted to 7 with a saturated aqueous solution of sodium hydrogen carbonate. The layers were separated and the organic layer washed sequentially with water and brine, dried with anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was dissolved in pentane and the solvent removed under reduced pressure again. This was then repeated, to afford the title compound as a slightly impure white solid (30.9 g).

Provenance & Evidence