Phosphoric Acid → HCID 18386604, compound

Participants

Reaction Steps

A mixture of 2-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-pyridin-3-ylmethyl]-malonic acid dimethyl ester (100 mg, 0.219 mmol), 85% phosphoric acid (3 ml) and water (3 ml) was heated at reflux for 2 hours. The reaction mixture was cooled to rt, diluted with water and neutralized to pH 6 with dilute NaOH and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to dryness to give 61 mg of a yellow foam. The oil was purified through silca gel column chromatography using 10% EtOAc in hexane as eluent to give 41 mg of the title compound as a tan solid, mp 44-46° C. 1H NMR (CDC13) δ 6.87(s,2H), 6.36(s,1H), 5.64(brs,1H), 4.21(m,1H), 2.51(m,2H), 2.37(m,2H), 2.29(s,3H), 2.27(s,3H), 2.11(s,6H), 2.02(m,2H), 1.76(m,2H), 0.86(t,6H) ppm.

Provenance & Evidence