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

Participants

Reaction Conditions

Reaction Steps

NaHMDS in THF (1.0 M, 11.0 mL, 11.0 mmol) was added over 30 min to a solution of 2,4,6-trimethylaniline (1.2 mL, 8.32 mmol) and 5-{2-[2-methoxy-4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl}-1-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (1.25 g, 2.77 mmol) in THF (30 mL) at 0° C. The resulting brown solution was stirred at 0° C. for 10 min and allowed to warm to room temperature over a period of 20 min. After stirring at room temperature for 4 h, the reaction was quenched by the addiction of saturated aqueous NH4Cl (10 mL). The reaction was partitioned between ethyl acetate (50 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic solution was washed with brine (50 mL), dried over Na2SO4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: dichloromethane/methanol 95/5) to afford 1.10 g (72% yield) of the title compound.

Provenance & Evidence