Triphenylphosphine → N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine

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Reaction Steps

(E)-di-tert-butyl diazene-1,2-dicarboxylate (321 mg, 1.39 mmol) was added slowly to a 0° C. well stirred solution of 3-methylbut-3-en-2-ol (100 mg, 1.16 mmol), triphenylphosphine (365 mg, 1.39 mmol) and N-(3-methyl-5-(1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine (371 mg, 1.16 mmol) in THF (3.5 mL). The reaction was stirred for 10 min and allowed to warm to RT for 18 hours. The reaction was quenched into aqueous potassium hydrogen sulfate (5%, 20 mL) and product extracted with ethyl acetate (2×20 mL). The organic extracts were combined dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10-50% ethyl acetate/hexanes) to afford N-(3-methyl-5-(1-(3-methylbut-3-en-2-yl)-1H-pyrazol-4-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amine MS ESI calcd. for C20H21F3N5 [M+H]+ 388. found 388.

Provenance & Evidence