p-Toluenesulfonic acid → HCID 22504340, compound

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Reaction Steps

A mixture of 3-[4-chloro-2-methyl-6-(2,4,6-trimethyl-phenylamino)-pyrimidin-5-yl]-2-methyl-propionic acid ethyl ester (173 mg, 0.46 mmol) and p-TsOH (56 mg) in 10 ml of toluene was heated at reflux using Dean-stark trap apparatus for 9 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic extract was washed with brine, dried and concentrated to give 184 mg of the crude material. The crude material was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 95 mg of the title compound as white crystals, mp 136-139° C., after recrystallization from ethyl ether. 1H NMR (CDCl3) δ 6.95(s,1H), 6.94(s,1H), 3.25(dd,1H), 2.8-3.0(m,2H), 2.41(s,3H), 2.32(s,3H), 1.96(s,3H), 1.93(s,3H), 1.37(d,3H)ppm.

Provenance & Evidence