Potassium Carbonate → 2-(Butyloxy)-9-(4-chlorobutyl)-8-(methyloxy)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate salt (for example, as prepared for Intermediate 6) (2 g, 5.69 mmol) and potassium carbonate (1.967 g, 14.23 mmol) were suspended in DMF (20 mL) and heated to 50° C., under nitrogen for 30 minutes. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (commercially available, for example, from Aldrich) (0.656 mL, 5.69 mmol) was added and stirring continued at room temperature for 20 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between DCM (40 mL) and water (40 mL). The layers were separated using a hydrophobic frit and the aqueous layer washed with DCM (10 mL). The combined organic extracts were concentrated in vacuo to give crude material that was purified by silica chromatography using the Flashmaster (70 g cartridge) eluting with a cyclohexane:ethyl acetate 0-100% gradient over 30 min. The product containing fractions were combined and evaporated to give the title compound as a white solid (1.4 g).

Provenance & Evidence