2,6-Diethylaniline → 5-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid (2,6-diethyl-phenyl)-amide

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-{2-[2-Methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-ethyl-1H-pyrrole-3-carboxylic acid (75 mg, 0.178 mmol) in anhydrous dimethylformamide (5 mL) was treated with N-ethyl-N,N-diisopropylamine (0.3 mL, 1.775 mmol) and TBTU (91 mg, 0.284 mmol). The mixture was then treated with 2,6-diethylaniline (0.3 mL, 1.775 mmol). The resulting mixture was stirred at 80° C. for 4 hours under argon. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (20 mL), washed with a saturated aqueous solution of sodium hydrogen carbonate (20 mL), brine, dried over anhydrous Na2SO4 and concentrated. Purification by flash chromatography on silica gel (eluant: dichloromethane/methanol 95/5) afforded 23 mg (23%) of the title compound.

Provenance & Evidence