Aniline → 3-(2,4-Diphenylamino-pyrimidin-5-yl)-2-pyridin-4-yl-propionic acid ethyl ester

Temperature

120 °C

A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-4-yl-propionic acid ethyl ester (0.68 g, 2.0 mmol) (from Example 9a supra) and aniline (3.0 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 then 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-pyridin-4-yl-propionic acid ethyl ester as a brown solid which was used in the next step without further purification. (Yield 0.54 g, 83.1%).

1. washThe reaction mixture was washed with hexanes (50 mL×3)
2. customthe supernatant was decanted off after each time
3. dissolutionThe residue was then dissolved in ethyl acetate (100 mL)
4. washsuccessively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude product was triturated with ethyl acetate-hexanes
9. filtrationThe resulting solid was collected by filtration
10. washwashed with diethyl ether

ORD record

ord-c8b46ff25274422d8d420363821a71ce

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07098332B2