Water → Ethyl 4-Dimethylcarbamoyl-2-[6-(3-ethyl-ureido)-pyridin-3-yl]-thiazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

In a 10 mL of microwave vial, 2-chloro-4-dimethylcarbamoyl-thiazole-5-carboxylic acid ethyl ester (Intermediate 26, 0.1 g, 0.37 mmol), N-ethyl-N′-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-yl]-urea (Intermediate1, 0.11 g, 0.37 mmol), cesium carbonate (0.12 g, 0.37 mmol), Tetrakis (triphenyl phosphino) palladium (0) (0.044 g, 0.037 mmol) in 4 mL of 4:1 dioxane:H2O was degassed for 30 min, then heated to 100° C. for 30 min. The reaction mixture was diluted with ethyl acetate (25 mL), then washed with water (10 mL). The organic layer was dried and concentrated to yield crude residue, which was purified by column chromatography over silica gel to afford 0.049 g (36.5%) of the title compound as a pale yellow solid. MS (APCI): 357 (M+H+) for C17H21N5O4S; NMR: δ 1.25 (t, 3H), δ 1.38 (t, 3H), δ 2.91 (s, 3H), δ 3.18 (s, 3H), δ 3.42 (q, 2H), δ 4.36 (q, 2H), δ 6.92 (d, 1H), δ 8.14 (d, 1H), δ 8.78 (d, 1H).

Provenance & Evidence