Hexane → 4-(tert-butyl)-N-[3-(2-[{5-chloro-2-pyrimidinyl}oxy]ethoxy)-1-(2-hydroxyethyl)-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Participants

Reaction Steps

A solution of 4-(tert-butyl)-N-[1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-(2-[{5-chloro-2-pyrimidinyl}oxy]ethoxy)-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Preparation 27) (90 mg) and tetrabutylammonium fluoride (1.0M in THF, 0.13 ml) in anhydrous THF (2 ml) was stirred for 3 hours at room temperature. After this period, tlc analysis (2:1 ethyl acetate:hexane) showed that little reaction had occurred. A second aliquot of 1.0M tetrabutylammonium fluoride in THF (0.13 ml) was added to the reaction solution and the resulting mixture was stirred at room temperature overnight. The reaction mixture was diluted with ether (30 ml) and then extracted with 1.0M citric acid (20 ml) and water (20 ml). The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a Biotage Flash 12i cartridge at 10 psi using 60% ethyl acetate/hexane as eluent to give the title compound as a colourless oil (56 mg).

Provenance & Evidence