Hydrochloric Acid → 4-[4-(Methylthio)phenyl]-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

HRID 1966356Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1966356
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:30][S:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.Cl>C1(C)C=CC=CC=1>[CH3:30][S:31][C:32]1[CH:37]=[CH:36][C:35]([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:5]=[C:4]([C:20]([F:23])([F:22])[F:21])[N:3]=2)=[CH:34][CH:33]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27339594-(Methylthio)phenylboronic acidHCID 104046804-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Produkt 1

HCID 249575454-[4-(Methylthio)phenyl]-5,6-diphenyl-2-(trifluoromethyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

4-Chloro-5,6-diphenyl-2-(trifluoromethyl)pyrimidine (0.2 g, 0.6 mmol, prepared according to the procedure described in PCT/IB03/02879) was heated to reflux with tetra-kis triphenyl palladium (0) (0.068 g, 0.058 mmol), aqueous solution of potassium carbonate (0.16 g in 0.6 ml water), 4-(methylthio)benzene boronic acid (0.168 g, 1 mmol) and toluene (20 ml) under a nitrogen atmosphere overnight. The reaction mixture was acidified with dilute hydrochloric acid 10 ml and extracted with ethyl acetate. The organic layer was concentrated; the crude material obtained was triturated with ether and filtered to yield the title compound. 1H-NMR (DMSO-d6) δ: 2.45 (s, 3H), 7.13-7.15 (m, 4H), 7.23-7.34 (m, 8H), 7.61 (d, 2H); MS m/z: 423.1 (M++1).

Aufarbeitung

  1. temperaturewas heated
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. customthe crude material obtained
  5. customwas triturated with ether
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-04a9014440d24d15a3f0b70c5c8e93cf
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420653B2

Notizen zur Reaktion

Wird geladen…