Réaction #87933

Équation de réaction

Methyliodide

3-bromo-4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

INTERMEDIATE 22

3-bromo-4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

cesium carbonate

Ethyl acetate

→

3-Bromo-4-[3-methyl-2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Lavagethe organic phase is washed with water three times
2. 2
   Séchagedried over MgSO4
3. 3
   Concentrationconcentrated
4. 4
   AutreThe crude product is purified by flash chromatography on silica (cyclohexane/ethyl acetate 30:70)
5. 5
   Autre0.70 min (X012_S02)

Mode opératoire

Methyliodide (3.55 mL, 57.1 mmol) is added to a mixture of 3-bromo-4-[2,5-dioxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4,5,6,7,8-octahydro-quinazolin-4-yl]-benzonitrile (INTERMEDIATE 22, 14.0 g, 28.6 mmol) and cesium carbonate (18.6 g, 57.1 mmol) in DMF (140 mL). The mixture is stirred at room temperature for 90 min. Ethyl acetate is added and the organic phase is washed with water three times, dried over MgSO4 and concentrated. The crude product is purified by flash chromatography on silica (cyclohexane/ethyl acetate 30:70). Yield: 13.4 g. ESI mass spectrum: [M+H]+=504 (bromine isotope pattern); Retention time HPLC: 0.70 min (X012_S02).

Source