Aniline → 2,5-Dimethoxy-phenyl propionic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

The mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-(2,5-dimethoxy-phenyl)-propionic acid ethyl ester (0.36 g, 0.94 mmol) (from Example 6a supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 2 hours. The reaction mixture was washed with hexanes (50 mL×3), and the supernatant was decanted off after each time. The residue was dissolved in ethyl acetate (100 mL) and successively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with ethyl acetate-hexanes. The resulting solid was collected by filtration and washed with diethyl ether to give 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-(2,5-dimethoxy-phenyl propionic acid ethyl ester as a yellow solid, which was used in the next step without further purification. (Yield 437.6 mg, 93.9%).

Provenance & Evidence