Tetrabutylammonium Fluoride → 1-Cyclopropyl-2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol

Participants

Reaction Steps

To a solution of 4-{5-[2-(tert-butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,6-dichloro-pyrimidin-4-yl}-morpholine (386 mg, 0.86 mmol) in THF (10 mL) was added TBAF (947 μL, 0.95 mmol, 1.0 M solution in THF) dropwise. The reaction mixture was stirred at RT for 3 hours before the reaction was quenched with saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (3×20 mL) and then combined organic phases were washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The resultant residue was purified by column chromatography (SiO2, gradient 0-50% ethyl acetate) giving 1-Cyclopropyl-2-(2,4-dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-ethanol as a colourless gum (196 mg, 68%). LCMS: RT=3.04 min, [M+H]+=334/336.

Provenance & Evidence