Hexane → 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline

HRID 507462

Reaktionsgleichung

CCCCCC.[CH3:7][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH3:9].[Br:15][C:16]1[CH:17]=[C:18]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29](F)=[C:30]([N+:33]([O-])=O)[CH:31]=3)[N:26]=[CH:25][N:24]=2)[CH:19]=[CH:20][CH:21]=1.CCOC(C)=O>C1COCC1.C(Cl)Cl.CCCCCC.CO.CCOC(C)=O>[NH2:33][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][C:29]=1[O:14][CH2:13][CH2:12][CH2:11][CH2:10][N:8]([CH3:9])[CH3:7])[N:26]=[CH:25][N:24]=[C:23]2[NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([Br:15])[CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 20 °C

Versuchsvorschrift

To a suspension of hexane prewashed sodium hydride (11.0 mmol, 440 mg of a 60% dispersion in mineral oil) in THF (20 mL) was cannulated a solution of 4-(N,N-dimethylamino)butan-1-ol (8.80 mmol, 1.03 g) in THF (30 mL). The resulting suspension was stirred at 20° C. under N2 for 2 hours and then cannulated into a solution of 4-[(3-bromophenyl)amino]-7-fluoro-6-nitroquinazoline (J Med Chem, 1996;39:918-928) (0.80 g, 2.20 mmol) in THF (30 mL) under N2. The dark red solution was then heated at reflux overnight. Identical workup as above gave, after chromatography on grade III alumina eluting with EtOAc to MeOH/EtOAc (5:95) to give 6-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline (310 mg, 33%) as a pale brown powder, mp (CH2Cl2/hexane) 155-156° C.

Aufarbeitung

temperatureThe dark red solution was then heated
temperatureat reflux overnight
customIdentical workup as above gave

Quellen und Nachweise

ORD-Eintrag: ord-aaa9a787be5245399bc02482bc78573d
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07786131B2

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