Reacción #1702127

ord-1af3814c846d43a3bc2e857f607f7351

Ecuación de reacción

COc1cccc(CCN)c1
3-methoxyphenethylamine
Clc1ncc(Cl)c(Cl)n1
2,4,5-trichloropyrimidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
COc1cccc(CCNc2nc(Cl)ncc2Cl)c1
desired product
Rendimiento 95.0%
COc1cccc(CCNc2nc(Cl)ncc2Cl)c1
2,5-Dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine
Rendimiento 95.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe reaction was quenched with water
  2. 2
    workup.ADDITIONEtOAc was added
  3. 3
    Otrothe layers were separated
  4. 4
    ExtracciónThe aqueous layer was extracted with EtOAc twice
  5. 5
    LavadoThe combined organic layers were washed with water and brine successively
  6. 6
    Secadodried (Na2SO4)
  7. 7
    Filtraciónfiltered
  8. 8
    Concentraciónconcentrated

Procedimiento

To a solution of 3-methoxyphenethylamine (1.93 mL, 13.2 mmol) and 2,4,5-trichloropyrimidine (1.59 mL, 13.9 mmol) in N,N-dimethylformamide (40 mL) was added potassium carbonate (5.5 g, 40 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated to give the desired product as a yellow gel (3.74 g, 95%). LCMS for C13H14Cl2N3O (M+H)+: m/z=298.0, 300.0.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08765727B2uspto-grants-2014_07