Reacción #4424

ord-dc411ea16f934b7bbc3fdf11d0029adc

Ecuación de reacción

COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(Cl)n2)cc1OC
2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine
C1CNCCN1
piperazine
COc1ccc(-c2cc(=Nc3c(C)cc(C)cc3C)n(C)c(N3CCNCC3)n2)cc1OC
3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine
Rendimiento 57.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaThe mixture was refluxed for 3 hours
  2. 2
    OtroThe mixture was evaporated
  3. 3
    workup.DISSOLUTIONthe residue was dissolved in chloroform
  4. 4
    Lavadowashed with aqueous sodium bicarbonate solution
  5. 5
    SecadoThe organic layer was dried over magnesium sulfate
  6. 6
    Otroevaporated
  7. 7
    OtroThe residue was chromatographed on silica gel using
  8. 8
    workup.ADDITIONa mixture of chloroform and methanol (95:5)

Procedimiento

To a suspension of 2-chloro-3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-(2,4,6-trimethylphenylimino)pyrimidine (1.07 g) in ethanol (10 ml) was added piperazine (0.70 g). The mixture was refluxed for 3 hours, cooled to ambient temperature. The mixture was evaporated, and the residue was dissolved in chloroform and washed with aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel using a mixture of chloroform and methanol (95:5) to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-2-(1-piperazinyl)-4-(2,4,6-trimethylphenylimino)pyrimidine (0.69 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04725600uspto-grants-1988_02