Réaction #1005947

ord-287538803f06481ea775b8ec999614cc

Équation de réaction

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
Rendement 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
Rendement 95.0%

Conditions de réaction

Température
100°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureAfter cooling
  2. 2
    Extractionextracted with ethyl acetate
  3. 3
    SéchageThe organic layer was dried over magnesium sulfate
  4. 4
    AutreThe solvent was evaporated off under reduced pressure
  5. 5
    Autrethe residue was then purified by a silica gel chromatography

Mode opératoire

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09271499B2uspto-grants-2016_03