Reaktion #66322

ord-426f1c2152a64c8bbebd23636fbb52b5

Reaktionsgleichung

O=S(=O)(c1ccccc1C(F)(F)F)[C@H]1CCNC1
(S)-3-(2-Trifluoromethyl-benzenesulfonyl)-pyrrolidine
CSc1nc(Cl)cc(C(F)(F)F)n1
4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine
[F-].[K+]
KF
CSc1nc(N2CC[C@H](S(=O)(=O)c3ccccc3C(F)(F)F)C2)cc(C(F)(F)F)n1
2-Methylsulfanyl-4-trifluoromethyl-6-[(S)-3-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidin-1-yl]-pyrimidine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was irradiated in the microwave oven at 150° C. for 1.5 h
  2. 2
    SonstigeThe reaction mixture was evaporated to dryness
  3. 3
    Sonstigepurified by flash chromatography (50 g silica gel, ethyl acetate/n-heptane:0:1→1:0)
  4. 4
    Sonstigeto yield a light yellow oil (790 mg; 94%)

Vorschrift

(S)-3-(2-Trifluoromethyl-benzenesulfonyl)-pyrrolidine (500 mg) was dissolved in acetonitrile (3.5 mL) in a microwave tube. 4-Chloro-2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidine (450 mg), TEA (0.75 mL) and KF (10 mg) were added. The reaction mixture was irradiated in the microwave oven at 150° C. for 1.5 h. The reaction mixture was evaporated to dryness and purified by flash chromatography (50 g silica gel, ethyl acetate/n-heptane:0:1→1:0) to yield a light yellow oil (790 mg; 94%) MS: m/z=472.2 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524710B2uspto-grants-2013_09