Réaction #10407

Équation de réaction

(3-chloro-2-cyclopropylamino-4,5-difluorobenzoyl)-hydrazinecarboxylic acid tert-butyl ester

potassium carbonate

triphosgene

tetrahydrofuran

→

title compound

(8-Chloro-1-cyclopropyl-6,7-difluoro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)carbamic acid tert-butyl ester

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture is refluxed for 90 minutes
2. 2
   LavageThe organic layer is washed with water and brine
3. 3
   Séchagedried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   ConcentrationThe filtrate is concentrated under vacuum
6. 6
   Autrepurified via flash column chromatography (1:2 ethyl acetate/hexanes)

Mode opératoire

To a solution of (3-chloro-2-cyclopropylamino-4,5-difluorobenzoyl)-hydrazinecarboxylic acid tert-butyl ester (Example 6c) (1.93 g, 5.34 mmol) in tetrahydrofuran (50 mL) is added potassium carbonate (3.69 g, 26.7 mol) and triphosgene (2.06 g, 6.95 mmol). The reaction mixture is refluxed for 90 minutes, cooled to room temperature, and diluted with ethyl acetate. The organic layer is washed with water and brine, then dried over MgSO4 and filtered. The filtrate is concentrated under vacuum and purified via flash column chromatography (1:2 ethyl acetate/hexanes) to afford the title compound (1.27 g). MS EI: m/z 386 (M+).

Source