Reacción #1005947

ord-287538803f06481ea775b8ec999614cc

Ecuación de reacción

CCOC(=O)c1cnc(Cl)nc1C(F)(F)F
Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate
FC(F)(F)C1(c2cc(Cl)c(Cl)c(Cl)c2)CCNC1
3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)c1cnc(N2CCC(c3cc(Cl)c(Cl)c(Cl)c3)(C(F)(F)F)C2)nc1C(F)(F)F
title compound
Rendimiento 95.0%
CCOC(=O)c1cnc(N2CCC(c3cc(Cl)c(Cl)c(Cl)c3)(C(F)(F)F)C2)nc1C(F)(F)F
ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)pyrimidine-5-carboxylate
Rendimiento 95.0%

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling
  2. 2
    Extracciónextracted with ethyl acetate
  3. 3
    SecadoThe organic layer was dried over magnesium sulfate
  4. 4
    OtroThe solvent was evaporated off under reduced pressure
  5. 5
    Otrothe residue was then purified by a silica gel chromatography

Procedimiento

Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (1.2 g) [see J. Med. Chem., 43, 3995 (2000)], 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine (1.5 g), and potassium carbonate (0.7 g) were added to N,N-dimethylformamide (50 mL) and the mixture was heated at 100° C. for 5 hours. After cooling, the reaction solution was poured over ice water, and then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (2.4 g, 95%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09271499B2uspto-grants-2016_03