Cesium carbonate → HCID 66742365, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyrazin-2-amine (prepared as in WO2004052869, Example 54, 175 mg, 0.90 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (200 mg, 0.90 mmol), cesium carbonate (1.02 g, 3.13 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (77.7 mg, 0.13 mmol) in dioxane (10 ml) was flushed with argon before tris(dibenzylideneacetone)dipalladium(0) (61.5 mg, 0.07 mmol) was added and the resulting solution was heated at 90° C. for 18 h. The mixture was cooled to room temperature and diluted with dichloromethane (50 mL) and water. The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The organic layers were combined, dried over magnesium sulfate. The resulting mixture was filtered and concentrated in vacuo. The precipitate formed was isolated by filtration, washed with ether and dried under vacuum to give 6-chloro-4-[5-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pyrazin-2-ylamino]-2-methyl-2H-pyridazin-3-one (150 mg, 50%) as a yellow solid.

Provenance & Evidence