Sodium Iodide → 2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[4-(tetrahydro-2H-pyran-4-ylamino)butyl]-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

9-(4-Chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine (70 mg, 0.205 mmol) was mixed with N,N-diisopropylethylamine (0.179 ml, 1.024 mmol), sodium iodide (30.7 mg, 0.205 mmol) and tetrahydro-2H-pyran-4-amine (62.1 mg, 0.614 mmol) in acetonitrile (1.5 ml) and heated at 70° C. under nitrogen overnight and then left at ambient temperature over the weekend. The acetonitrile was evaporated under nitrogen and the residue partitioned between aqueous sodium bicarbonate and dichloromethane. The aqueous phase was re-extracted with dichloromethane and the combined organic extracts were passed through a hydrophobic frit and evaporated under nitrogen to give an amber oil. This material was dissolved in 1:1 DMSO:MeOH (2×1 ml) and purified in two injections by Mass Directed AutoPrep (Method A). Product containing fractions were combined evaporated under nitrogen in a blowdown unit to give the title compound as a colourless oil (30.35 mg).

Provenance & Evidence