1: 1-cyclopropyl-6,7-difluoro-8-methoxy-1H-quinazoline-2,4-dione With sodium hydride in 1,4-dioxane; N,N-dimethyl-formamide; mineral oil T=2 - 72°C; 2: O-(4-nitrophenyl)hydroxylamine in 1,4-dioxane; N,N-dimethyl-formamide; mineral oil T=72°C; 20 h; Reagent/catalystTemperatureTime;

potassium carbonate in 1,4-dioxane; N,N-dimethyl-formamide T=70 - 72°C; 20 h;

N-hydroxy-2,4-dinitrobenzenamine; sodium hydride in tetrahydrofuran 1.5 h; Heating;

1.1: 1,2-dichloro-ethane / 4 h / Heating 1.2: 90 percent / dioxane / 4 h / 0 - 20 °C 2.1: 84 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 1.5 h / Heating 3.1: 89 percent / sodium hydride; (2,4-dinitro-phenyl)-hydroxylamine / tetrahydrofuran / 1.5 h / Heating View Scheme

1.1: oxalyl chloride; N,N-dimethylformamide / CH2Cl2 / 1.5 h / 20 °C 1.2: 100 percent / ammonia gas / CH2Cl2 / 2 h / 0 °C 2.1: 1,2-dichloro-ethane / 4 h / Heating 2.2: 90 percent / dioxane / 4 h / 0 - 20 °C 3.1: 84 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 1.5 h / Heating 4.1: 89 percent / sodium hydride; (2,4-dinitro-phenyl)-hydroxylamine / tetrahydrofuran / 1.5 h / Heating View Scheme

1: ammonia / tetrahydrofuran / 1.17 h / -50 - 20 °C 2: oxalyl dichloride / 1,2-dichloro-ethane / 24 h / 20 °C / |Reflux 3: dichloromethane / -6 - 20 °C 4: sodium hydride / toluene; ethylene glycol dimethyl ether; mineral oil / 24.5 h / -4 °C / |Reflux 5: potassium carbonate / N,N-dimethyl-formamide; 1,4-dioxane / 20 h / 70 - 72 °C View Scheme

1: 84 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 1.5 h / Heating 2: 89 percent / sodium hydride; (2,4-dinitro-phenyl)-hydroxylamine / tetrahydrofuran / 1.5 h / Heating View Scheme