Sodium Carbonate → N-(6-(2-amino-6-methylpyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of tetrakis(triphenylphosphine)palladium (0) (0.115 g, 0.0999 mmol), 4-chloro-6-methylpyrimidin-2-amine (0.142 g, 0.999 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (0.318 g, 0.999 mmol) under nitrogen was added sodium carbonate (1 mL, 2M in water, 2 mmol) and then 1,4-dioxane (6 mL). The flask was heated in a pre-heated (90° C.) bath and stirred under an inert atmosphere overnight. The mixture was allowed to cool to ambient temperature and concentrated. The crude material was diluted with DCM and washed with brine. The organic layer was dried over sodium sulfate, concentrated, and purified by silica gel chromatography (0-10% MeOH in DCM) to give N-(6-(2-amino-6-methylpyrimidin-4-yl)benzo[d]thiazol-2-yl)acetamide (200 mg, 67%) as a brown solid. MS (ESI pos. ion) m/z: 300 (MH+). Calculated exact mass for C14H13N5OS: 299.

Provenance & Evidence