Tetrabutylammonium Fluoride → HCID 68686088, compound

Participants

Reaction Steps

208 mg of the 2-{[1-(4-{[t-butyl(diphenyl)silyl]oxy}phenyl)ethyl]amino}-4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-5-carbonitrile [111-1] was dissolved in 5 mL of tetrahydrofuran, then 320 μL of tetrabutylammonium fluoride (1.0M tetrahydrofuran solution) was added under an ice-cold condition, and stirred at room temperature for 1 hour. The reaction solution was diluted in 200 mL of ethyl acetate, and washed with phosphate buffer pH6.8 and saturated brine in the subsequent order. The obtained organic layer was dried over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in a small amount of mixture solvent of chloroform and methanol (chloroform:methanol=9:1) and solidified by hexane, to obtain 107 mg of 4-[8-(difluoromethyl)imidazo[1,2-a]pyridin-3-yl]-2-{[1-(4-hydroxyphenyl)ethyl]amino}pyrimidine-5-carbonitrile [111-2] as a white solid.

Provenance & Evidence