Diisobutylaluminumhydride → HCID 58764268, compound

Participants

Reaction Steps

To a solution of imidazo[1,2-b][1,2,4]triazine-6-carboxylic acid ethyl ester (500 mg, 2.6 mmol, from step 1 above) in CH2Cl2 (15 mL) cooled to −78° C. was added diisobutylaluminum hydride (2.6 mL, 1.5 M in toluene). The reaction was stirred for one hour, and then extra diisobutylaluminum hydride (1 mL, 1.5 M) was added. After 20 more minutes, the cold reaction was quenched with EtOAc (10 mL), and then MeOH (10 mL). After the reaction had warmed to room temperature, 30 mL of 0.3 M HCl was added. The layers were separated. The aqueous phase was extracted three times with 10 mL of CH2Cl2. After the organic layers were combined and dried over MgSO4, the solids were removed by filtration. The organic liquid was concentrated by rotary evaporation, and the resulting oil was chromatographed (40 g SiO2, 50 to 100% EtOAc in hexanes) to give the desired product (47 mg, 12%).

Provenance & Evidence