Cesium carbonate → HCID 59519096, compound

Participants

Reaction Conditions

Reaction Steps

Racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (5 mg, 0.009 mmol) and anhydrous toluene (0.5 mL) was heated in a microwave vial with stirring at 80° C. under an Argon atmosphere until a homogeneous milky solution was obtained (˜5 min). This solution was cooled to room temperature and palladium(II) acetate (2 mg, 0.006 mmol) was added. After stirring at room temperature for 2 min., 2-[6-bromo-2-(3-chlorophenyl)-4-oxo-4H-quinazolin-3-yl]-N-tert-butylacetamide (INTERMEDIATE VI.1) (67 mg, 0.15 mmol), tert-butyl-1-homopiperazinecarboxylate (35 μL, 0.18 mmol) and freshly ground cesium carbonate (68 mg, 0.21 mmol) were added to the red solution. Anhydrous dioxane (0.2 mL) was added to rinse down solid left on the side of the vial. The vial was capped and heated in a microwave at 120° C. for 40 min. The reaction mixture was diluted with DCM (3 mL), filtered and the filtrate concentrated in vacuo. This crude product was purified by preparative TLC on silica gel with hexane:EtOAc:CH2Cl2 (1:1:1, v/v) as eluent to give 4-[3-(tert-butylcarbamoylmethyl)-2-(3-chlorophenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]perhydro-1,4-diazepine-1-carboxylic acid tert-butyl ester (INTERMEDIATE VIII.1) (38.9 mg, 0.07 mmol, 46%) as a yellow solid.

Provenance & Evidence