Ammonia → 2-Chloro-9-(tetrahydropyran-2-yl)adenine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichloropurine (25 g) (commercially available from, for example, Aldrich) in dry ethyl acetate (200 mL) was added p-toluenesulfonic acid monohydrate (235 mg) (commercially available from, for example, Aldrich). The reaction was heated to 50° C. and 3,4-dihydro-2H-pyran (18.1 ml) (commercially available from, for example, Aldrich) was added in one go. The reaction was allowed to stir at 50° C. for 1 hour and the solvent was removed under reduced pressure. This afforded a yellow solid. A suspension of this solid (˜36 g) in 2.0M ammonia in isopropanol (460 mL) was heated under nitrogen at 60° C. for 4 hours with an attached condenser. The reaction was poured into water (50 mL) and left to cool overnight. The precipitate was filtered and dried on a rotary evaporator (60° C.) for 30 minutes to afford the title compound as an off-white solid, 31 g (93%, 2 steps).

Provenance & Evidence