3-Bromo-3'-(trifluoromethyl)benzanilide → 3-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamide

HRID 338743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338743
Br[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].[CH3:21][S:22][C:23]1[N:24]=[CH:25][C:26]2[CH2:32][NH:31][CH2:30][CH2:29][C:27]=2[N:28]=1.CC(C)([O-])C.[Na+]>C1COCC1.CCOC(C)=O.CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C>[CH3:21][S:22][C:23]1[N:24]=[CH:25][C:26]2[CH2:32][N:31]([C:2]3[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=3)[C:5]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=3)=[O:6])[CH2:30][CH2:29][C:27]=2[N:28]=1

Komponenten

7

Edukt 3

HCID 7638833-Bromo-3'-(trifluoromethyl)benzanilideHCID 23676156Sodium t-butoxideHCID 552636702-(Methylthio)-5,6,7,8-tetrahydropyrido[4,3-D]pyrimidine

Produkt 1

HCID 717356913-[2-(methylthio)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-N-[3-(trifluoromethyl)phenyl]benzamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylKatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-bromo-N-[3-(trifluoromethyl)phenyl]benzamide (379 mg, 1.10 mmol), 2-(methylsulfanyl)-5,6,7,8-tetrahydropyrido[4,3-d]-pyrimidine (200 mg, 1.10 mmol), RuPhos (15.4 mg, 0.033 mmol), Cl—RuPhos-Pd precatalyst (24 mg, 0.033 mmol), and sodium-t-butoxide (148 mg, 1.54 mmol) in anhydrous THF (30 ml) was heated at 80° C. under nitrogen for 21 hours. Upon cooling, the reaction mixture was diluted with EtOAc and the insolubles were filtered off (celite). The filtrate was concentrated and the residue was eluted through a flash column (silica gel 60, 230-400 mesh, 1:1 hexanes:EtOAc) to obtain a yellow, crystalline solid (389 mg, 80%).

Aufarbeitung

  1. temperatureUpon cooling
  2. filtrationthe insolubles were filtered off (celite)
  3. concentrationThe filtrate was concentrated
  4. washthe residue was eluted through a flash column (silica gel 60, 230-400 mesh, 1:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4649514306b84d4aa43865df107b4beb
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889870B2

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