Reacción #344968

Ecuación de reacción

Water

2-(3-Nitroanilino)-3-carbamoylpyridine

Sodium hydride

CDI

→

1-N-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Rendimiento 54.7%

Disolventes

EtOAc Et2O

tetrahydrofuran

—

hexanes

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadded to the solution
2. 2
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 1 hour
3. 3
   Temperaturasubsequently refluxed for 24 hours
4. 4
   OtroThe solvent was removed
5. 5
   Otroresulting in a brown residue
6. 6
   Extracciónthe resulting solution was extracted with ethyl acetate (5×300 ml)
7. 7
   OtroThe phases were separated

Procedimiento

2-(3-Nitroanilino)-3-carbamoylpyridine (20 g, 77.5 mmole) was dissolved in tetrahydrofuran (2000 ml). Sodium hydride (60% dispersion in oil) (12.4 g, 310.0 mmole) was washed in hexanes and added to the solution. The solution was stirred for 5 minutes at room temperature under an inert atmosphere. To the solution, CDI (1,1'-carbonyldiimidazole) (18.8 g, 116.2 mmole) was added in a gradual manner over a period of 15 minutes, the resulting mixture was stirred at room temperature for 1 hour and subsequently refluxed for 24 hours. The solvent was removed resulting in a brown residue. Water was added to the residue and the resulting solution was extracted with ethyl acetate (5×300 ml). The phases were separated and the product was recrystallized from EtOAc/Et2O yielding a 12 g (42.4 mmole, 54.5% yield) of 1-N-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (mp 262°-263° C.).

Fuente