1,3-Dibromopropane → 2-(Butyloxy)-8-(methyloxy)-9-{3-[(tetrahydro-2-furanylmethyl)amino]propyl}-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (70 mg, 0.2 mmol) and K2CO3 (68.8 mg, 0.050 mmol) was stirred in DMF (2 ml) at 50° C. for 1 hour. The reaction was cooled and 1,3-dibromopropane (0.020 ml, 0.2 mmol) was added. The mixture was stirred at 20° C. for 40 mins. (Tetrahydro-2-furanylmethyl)amine (0.41 ml, 0.2 mmol) and triethylamine (0.056 ml, 0.4 mmol) in DMF (1 ml) was added and the reaction mixture stirred at rt for 16 hours. Water (2 ml) and brine (2 ml) were added to the mixture. The product was extracted with DCM (2×5 ml) using a hydrophobic separation cartridge and the solvent removed on the N2 blowdown unit. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen to give the title compound as a white solid (20 mg).

Provenance & Evidence