Sodium Carbonate → N-(4-(4-(5-methylthiazol-2-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)cyclopropanecarboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of N-(4-(4,6-dichloropyrimidin-2-ylthio)phenyl)cyclopropane-carboxamide (5.0 g, 14.7 mmol), amino-5-methylthiazole (1.85 g, 16.2 mmol), tris(dibenzylideneacetone)dipalladium (0.673 g, 0.74 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-xanthene (0.636 g, 1.10 mmol) and sodium carbonate (2.18 g, 20.58 mmol) in dioxane (120 ml) was heated at 100° C. for 2 h. The reaction mixture was then allowed to cool to room temperature before the tan precipitate was collected by filtration, washed with ethyl acetate (50 ml) water (3×30 ml) and then diethyl ether (50 ml) and dried to give title compound as a tan solid (4.32 g, 70%). 1H NMR (DMSO) 0.81 (4H, d), 1.83 (1H, m), 2.09 (3H, s), 6.35 (1H, br s), 6.88 (1H, s), 7.53 (2H, d), 7.74 (2H, d), 10.48 (1H, s). MS (ES+): 418.

Provenance & Evidence