Tetrahydrofuran → 2-[4-(4-Fluorobenzoyl)benzylthio]-3,5-dimethyl-quinazolin-4-one

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Reaktionsgleichung

[SH:1][C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH3:14])[N:3]=1.C1COCC1.[OH-].[Na+].[F:22][C:23]1[CH:38]=[CH:37][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1>C(O)C.C(OCC)(=O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([C:27]([C:29]2[CH:36]=[CH:35][C:32]([CH2:33][S:1][C:2]3[N:11]([CH3:12])[C:10](=[O:13])[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][C:8]=4[CH3:14])[N:3]=3)=[CH:31][CH:30]=2)=[O:28])=[CH:37][CH:38]=1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of 2-mercapto-3,5-dimethylquinazolin-4-one (0.492 g) as obtained in Reference Example 18-in ethanol (10.0 ml)-THF (10.0 ml) was added 1N-sodium hydroxide (2.50 ml). Then, 4-(4-fluorobenzoyl)benzyl bromide (0.700 g) was added and the mixture was stirred at 60° C. for 3.5 hours. This reaction mixture was diluted with ethyl acetate and washed with saturated aqueous NaCl solution and the organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to provide the title compound as colorless needles (0.717 g, yield 72%). 1H-NMR (CDCl3) δ: 2.85(3H,s), 3.55(3H,s), 4.60(2H,s), 7.10-7.20(3H,m), 7.46-7.63(4H,m), 7.72-7.87(4H,m).

Aufarbeitung

washwashed with saturated aqueous NaCl solution
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-9016e0357b644b1f97896df44b913a0e
Quelldatensatz: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05753664

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