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

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Reaction Steps

To 4-(tert-butyl)-N-[3-(2-hydroxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]benzenesulfonamide (Example 2) (196 mg) in tetrahydrofuran (2.5 ml) at room temperature under an atmosphere of nitrogen was added sodium hydride (60% dispersion in oil, 37 mg) and the mixture was stirred for 5 minutes. To the mixture was added a solution of 5-chloro-2-methylsulphonylpyrimidine (94 mg) in tetrahydrofuran (5 ml) and dimethylacetamide (0.5 ml) the mixture was stirred for a further 48 hrs. The reaction was diluted with water (200 ml) and extracted with dichloromethane (3×50 ml). The organic fractions were combined, washed with brine (100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (20 g) eluted with ether:hexane (4:1) to yield the title compound as a white solid (170 mg).

Provenance & Evidence