1,3-Dibromopropane → HCID 67224004, compound

Participants

Reaction Conditions

Reaction Steps

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (70 mg, 0.199 mmol) was stirred with K2CO3 (68.9 mg, 0.498 mmol) in DMF (1 ml) for 1 hour at 50° C. The reaction mixture was cooled and 1,3-dibromopropane (0.020 ml, 0.199 mmol) was added. The reaction mixture was stirred at 20° C. for 40 mins. (3S)-Tetrahydro-3-furanamine hydrochloride (49.3 mg, 0.399 mmol) was shaken with aqueous NaOH solution (0.996 ml, 1.993 mmol) for 5 mins., DCM, (2×3 ml) was added and the mixture passed through a phase separation cartridge. The solvent was removed under mild conditions by rotary evaporation. The free base was added to the reaction mixture followed by triethylamine (0.056 ml, 0.399 mmol) and the mixture was stirred at 20° C. for 16 hours. (3S)-Tetrahydro-3-furanamine hydrochloride (49.3 mg, 0.399 mmol) was shaken with NaOH (0.996 ml, 1.993 mmol) for 5 mins., DCM (2×3 ml) was added, and the mixture passed through a phase separation cartridge and added directly to the reaction mixture. Triethylamine (0.056 ml, 0.399 mmol) was added and the mixture was stirred at 20° C. for 16 hours. Water was added and the mixture extracted with DCM (2×5 ml) through a hydrophobic frit. The solvent was removed by nitrogen blowdown. The samples were 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 (3 mg).

Provenance & Evidence