Triethylamine → tert-Butyl 4-(5-(4-amino-5-((benzyloxy)methyl)-2-butyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)pent-4-yn-1-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-((benzyloxy)methyl)-2-butyl-7-(5-chloropent-1-yn-1-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine (100 mg, 0.243 mmol) in anhydrous N,N-dimethylformamide (2 mL) was added 1-BOC-piperazine (50 mg, 0.268 mmol) and triethylamine (51 νL, 0.366 mmol). The reaction was stirred at 70° C. for 22 hours. A further 100 mg (0.537 mmol) of 1-BOC-piperazine and 0.1 mL (0.717 mmol) of triethylamine was added to the reaction. The reaction was stirred at 70° C. for a further 24 hours. The cooled reaction was evaporated in vacuo and partitioned between dichloromethane and water. The organic layer was passed through a hydrophobic frit and evaporated in vacuo to yield a yellow oil. The oil was dissolved in MeOH:DMSO (1:1) (2×1 mL) and purified by MDAP (Method B). Appropriate fractions were combined and evaporated in vacuo to yield the title compound as a colourless oil (80 mg).

Provenance & Evidence