Reacción #91400

Ecuación de reacción

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

phosphorus (V) oxychloride

→

titled compound

Rendimiento 74.0%

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

Rendimiento 74.0%

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente