Reaktion #11883

Reaktionsgleichung

3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester

aniline

→

3-(2,4-diphenylamino-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction mixture was washed with hexanes (50 mL×3)
2. 2
   Sonstigethe supernatant was decanted off after each time
3. 3
   workup.DISSOLUTIONThe residue was then dissolved in ethyl acetate (100 mL)
4. 4
   Waschensuccessively washed with saturated aqueous ammonium chloride solution (30 mL), water (30 mL) and brine (30 mL)
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe crude product was purified by preparative thin layer chromatography

Vorschrift

A mixture of 3-(2,4-dichloro-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester (326 mg, 1.0 mmol) (from Example 10a supra) and aniline (2.0 mL) (Aldrich) was heated at 120° C. for 1 hour. 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 purified by preparative thin layer chromatography to give 3-(2,4-diphenylamino-pyrimidin-5-yl)-2-pyridin-3-yl-propionic acid ethyl ester as a brown solid which was used in the next step without further purification. (Yield 60 mg, 13.7%).

Quelle