Potassium Carbonate → 2-(Butyloxy)-9-{2-[1-(1-methylethyl)-4-piperidinyl]ethyl}-8-(methyloxy)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (250 mg, 0.684 mmol) and potassium carbonate (236 mg, 1.711 mmol) were dissolved in DMF (4 ml) and heated at 60° C. for 1 hour. The reaction mixture was cooled to room temperature and phenylmethyl 4-(2-bromoethyl)-1-piperidinecarboxylate (223 mg, 0.684 mmol) added. The reaction was then heated to 50° C. for a further 18 hours. Phenylmethyl 4-(2-bromoethyl)-1-piperidinecarboxylate (45 mg, 0.147 mmol) was added and the reaction heated at 50° C. for a further 18 hours. The reaction mixture was diluted with DCM (5 ml) and water (5 ml) and the layers separated using a hydrophobic frit. The aqueous was washed with further DCM (5 ml) and the combined organics concentrated. The residue was purified by column chromatography, the sample was loaded in dichloromethane onto silica (Si) 20 g and eluted using a gradient of 0-100% ethyl acetate in cyclohexane+0-20% methanol over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow glass (114 mg).

Provenance & Evidence