Sodium Methoxide → 8-methoxy-2-(((S)-pentan-2-yl)oxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

8-Bromo-2-{[(1S)-1-methylbutyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (for example, as prepared for Intermediate 5) (7.1 g, 18.48 mmol) was dissolved in anhydrous methanol (70 mL) and a solution of sodium methoxide (25%) in methanol (8 mL) was added dropwise under an atmosphere of nitrogen. The solution was heated to reflux at 90° C. for 4 hours under an atmosphere of nitrogen. Additional sodium methoxide in methanol (25% solution, 3 mL) was added and the reaction was stirred at 60° C. for a further 16 hours. An additional portion of sodium methoxide in methanol (25% solution, 5 mL) was added and the reaction was stirred at 90° C. for a further 7 hours. The solvent was removed on the rotary evaporator and the crude product was partitioned between ethyl acetate (75 mL) and saturated ammonium chloride solution (75 mL). The organic layer was washed with brine (75 mL). The solvent was removed on the rotary evaporator to yield the title compound as a pale orange foam (6 g).

Provenance & Evidence