Reaktion #91400

Reaktionsgleichung

5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one

phosphorus (V) oxychloride

→

titled compound

Ausbeute 74.0%

4-chloro-5,6-dimethyl-N-(pyridin-2-ylmethyl)pyrimidin-2-amine

Ausbeute 74.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed overnight under nitrogen
2. 2
   SonstigeThen excess phosphorus (V) oxychloride was removed under reduced pressure
3. 3
   workup.ADDITIONToluene (30 mL) was added
4. 4
   Sonstigethe reaction mixture was evaporated under reduced pressure
5. 5
   workup.ADDITIONThe residue was diluted with 5% aqueous sodium bicarbonate (100 mL)
6. 6
   Extraktionextracted with ethyl acetate (2×200 mL)
7. 7
   SonstigeThe solvent was evaporated under reduced pressure
8. 8
   Wascheneluted with hexane/ethyl acetate (2:1)

Vorschrift

A solution of 5,6-dimethyl-2-[(pyridin-2-ylmethyl)amino]pyrimidin-4(3H)-one (7.0 g, 32.6 mmol, Step B) in phosphorus (V) oxychloride (30 mL) with addition of 1 drop of dimethylformamide was refluxed overnight under nitrogen. Then excess phosphorus (V) oxychloride was removed under reduced pressure. Toluene (30 mL) was added, and the reaction mixture was evaporated under reduced pressure. The residue was diluted with 5% aqueous sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×200 mL). The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography eluted with hexane/ethyl acetate (2:1). The titled compound 6.1 g (74%) was obtained as a light-yellow solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.10 (s, 3H), 2.39 (s, 3H), 4.54 (s, 2H), 7.20-7.30 (m, 2H), 7.68-7.76 (m, 2H), 7.76 (bs, 1H).

Quelle