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

HRID 251435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251435
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-d052a092758545628b1d2549e5d1f98c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863446B2

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