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

Participants

Reaction Conditions

Reaction Steps

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (100 mg, 0.285 mmol) and K2CO3 (98 mg, 0.712 mmol) was stirred in DMF (2 ml) at 50° C. for 1 hour. The reaction was cooled and 1,3-dibromopropane (0.029 ml, 0.285 mmol) was added. The mixture was stirred at 20° C. for 40 mins. (3R)-Tetrahydro-3-furanamine hydrochloride (35.2 mg, 0.285 mmol) and N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (146 mg, 0.854 mmol) were stirred in DMF 1 ml at 20° C. for 40 mins. The resultant mixture of assumed free base was added to the first reaction vessel and the mixture stirred for 16 hours at 20° C. 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 (7 mg).

Provenance & Evidence