Trimethylaluminum → HCID 20161352, compound

Participants

Reaction Steps

To a solution of 5-[N-(n-butyl)-2-oxo-3-pyrrolin-4-yl]amino-1-(pent-3-ynyl)-4-cyanopyrazole (0.88 g.) in dry dichloromethane (20 ml.) was added a solution of trimethylaluminium in heptane (4.2 ml. of a 1.35 M solution) while stirring at room temperature under nitrogen. After stirring overnight, the reaction was quenched by the cautious addition of 3N aqueous hydrochloric acid until gas evolution had ceased. The precipitated aluminium salts were solubilized by addition of a 10% w/v aqueous solution of sodium hydroxide and the product was extracted into EtOAc. The extract was washed with 10% w/v aqueous sodium hydroxide solution and then brine, dried (Na2SO4), and evaporated to leave a light yellow solid. Recrystallization from toluene/hexane gave the title compound as a white crystalline powder (0.5 g.): m.p. 171°-172.5°.

Provenance & Evidence