Triethylamine → (S)-9-(5-chloropentyl)-8-methoxy-2-(pentan-2-yloxy)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine, trifluoroacetate salt (600 mg, 1.642 mmol) (for example, as prepared for Intermediate 7) and potassium carbonate (567 mg, 4.11 mmol) were stirred at 60° C. in DMF (10 mL) for 1 hour under nitrogen. The reaction was cooled to room temperature when 1-bromo-5-chloropentane (commercially available, for example, from Aldrich) (0.216 mL, 1.642 mmol) and triethylamine (0.343 mL, 2.464 mmol) were added and the mixture stirred at 20° C. under nitrogen for 16 hours. The mixture was then diluted with water (10 mL) and brine (10 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were evaporated and the residue dissolved in dichloromethane and purified by column chromatography using the Flashmaster II (70 g aminopropyl cartridge) with a 0-100% ethyl acetate in cyclohexane gradient over 40 minutes. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow gum (430 mg).

Provenance & Evidence