Ethanol → HCID 69710392, compound

Participants

Reaction Steps

A mixture of tert-butyl 4-chloro-2-methylthio-5,6,7,8-tetrahydropyridino[4,3-d]pyrimidine-6-carboxylate (334 mg, 1.06 mmol), 2,4-dichlorobenzeneboronic acid (222 mg, 1.16 mmol), bis(dibenzylideneacetone)palladium(0) (48 mg, 0.053 mmol) and 1,4-bis(diphenylphosphino)butane (45 mg, 0.11 mmol) in toluene (2 ml), aqueous 1M sodium carbonate solution (1 ml) and ethanol (0.5 ml) was heated under reflux for 19 h under nitrogen. The reaction mixture was then cooled, water was added, and the toluene layer was separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were dried (MgSO4), filtered, and the filtrate concentrated in vacuo. The crude product was purified by column chromatography using 15% acetone in hexanes as eluent, giving tert-butyl 4-(2,4-dichlorophenyl)-2-methylthio-5,6,7,8-tetrahydropyridino[4,3-d]pyrimidine-6-carboxylate (471 mg, yield>100%) as a light yellow sticky foam.

Provenance & Evidence