Sodium hydride → 4-(tert-butyl)-N-[3-{2-[(5-methylthio-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide

Participants

Reaction Steps

To 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Example 2, 743 mg) in tetrahydrofuran (25 ml) at 0° C. under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 141 mg), the reaction mixture was stirred for 5 minutes. A solution of 2-chloro-5-(methylthio)pyrimidine (269 mg) in dimethyl acetamide (5 ml) was added and the reaction mixture allowed to warm up to room temperature. The reaction mixture was stirred for a further 2 hours. The reaction mixture was poured cautiously into a stirred bi-phasic solution of saturated aqueous ammonium chloride solution (100 ml) and ethyl acetate (100 ml). The organic fraction was separated, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (140 g) eluted with ethyl acetate:hexane (1:1) to yield the title compound as a yellow oil (921 mg).

Provenance & Evidence