Ammonium formate → 7-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

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Reaktionsgleichung

C([O-])=O.[NH4+].Br[C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([N+:17]([O-])=O)[C:15]=1[CH3:16])[N:12]=[CH:11][N:10]=[C:9]2[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1>C(O)C.[Pd]>[CH3:16][C:15]1[C:14]([NH2:17])=[C:13]2[C:8]([C:9]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

To a microwave vial were added ammonium formate (131 μl, 2664 μmol), 6-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine (569 mg, 1332 μmol), and palladium black (11.8 μl, 1332 μmol) in ethanol (10 mL). The reaction mixture was heated to 140° C. for 20 min under microwave conditions and taking care to monitor the pressure in the reaction vessel. On cooling the reaction mixture was filtered through celite and filtrate concentrated in vacuo to afford 7-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (238 mg, 56.1% yield). MS (M+H)+ 319.

Aufarbeitung

temperatureOn cooling the reaction mixture
filtrationwas filtered through celite and filtrate
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-059ca40293fa4bc987c316afc264965d
Quelldatensatz: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07989461B2

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