Triethylamine → HCID 118453797, compound

Participants

Reaction Steps

To a degassed solution of 5-((benzyloxy)methyl)-2-butyl-7-iodo-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-4-amine (159 mg, 0.353 mmol) in anhydrous N,N-dimethylformamide (3 mL) under a nitrogen atmosphere at room temperature was added copper (I) iodide (19 mg, 0.100 mmol), bis(triphenylphosphine)palladium(II)dichloride (40 mg, 0.057 mmol) and finally triethylamine (0.088 mL, 0.636 mmol). The mixture was stirred at room temperature under a nitrogen atmosphere for 10 minutes and then a solution of 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine (110 mg, 0.565 mmol) in anhydrous degassed N,N-dimethylformamide (1 mL) was added. The reaction mixture was stirred at 55° C. for 40 minutes. Additional 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine (110 mg, 0.565 mmol) was added and the reaction mixture was left to stir at 55° C. for 4 5 minutes. 1-(1-methylethyl)-4-(4-pentyn-1-yl)piperazine (110 mg, 0.565 mmol) was added and the reaction mixture was left to stir at 55° C. for 45 minutes. The reaction was evaporated in vacuo to yield a dark yellow oil. The oil was partitioned between water and dichloromethane. The organic layer was separated and the aqueous back extracted with dichloromethane. The combined organic extracts were passed through a hydrophobic frit and evaporated in vacuo to yield a dark yellow oil. The crude product was dissolved in 6 mL of 50:50 DMSO/MeOH and purified by MDAP (Method B). Fractions which contained product were concentrated to give the title compound as a yellow oil (61 mg).

Provenance & Evidence