Reacción #8605

Ecuación de reacción

1-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-butyn-1-one

N-phenylguanidine nitrate

potassium carbonate

→

4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-phenyl-2-pyrimidinamine

Rendimiento 36.0%

Disolventes

1-methyl-2-pyrrolidinone

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo to a syrup
2. 2
   workup.ADDITIONEthyl acetate and water were added
3. 3
   Otrothe phases separated
4. 4
   SecadoThe organic phase was dried (magnesium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated to a solid
7. 7
   OtroThis solid was crystallized from acetonitrile

Procedimiento

To a solution of 1-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-2-butyn-1-one (1.0 g, 3.36 mmol) in 1-methyl-2-pyrrolidinone (4 mL) was added N-phenylguanidine nitrate (1.0 g, 5.0 mmol) and anhydrous potassium carbonate (0.7 g, 5.0 mmol). The resulting mixture was heated at 150° C. for 12 hours and concentrated in vacuo to a syrup. Ethyl acetate and water were added and the phases separated. The organic phase was dried (magnesium sulfate), filtered and concentrated to a solid. This solid was crystallized from acetonitrile to give 500 mg (36%) of 4-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-phenyl-2-pyrimidinamine as a yellow solid. 1H-NMR (CDCl3): δ 8.48 (d, 1H), 8.45 (d, 1H), 8.23 (d,1H), 7.64 (m, 4H), 7.42 (t, 2H), 7.1–7.25 (m, 4H), 6.93 (dd, 1H), 6.52 (d, 1H); 19F-NMR (CDCl3): δ−112.29; MS m/z 416 (M+1).

Fuente