Cesium carbonate → HCID 58456133, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing 2,5-dichloropyrimidine (2 g, 13.42 mmol), 3-methyl-5-(1,3-thiazol-5-yl)aniline (2.55 g, 13.42 mmol), PdOAc2 (0.603 g, 2.68 mmol), Xantphos (2.330 g, 4.03 mmol), and cesium carbonate (8.75 g, 26.8 mmol) was degassed for 5 min. Dioxane (89 ml) was added and argon was bubbled through the mixture for 15 min. The temperature was increased to 110° C. and the reaction was stirred 14 h at that temperature. The cooled reaction was diluted with brine and water and extracted three times with CH2Cl2. The organic layer was concentrated under reduced pressure and purified by flash chromatography (0-70% EtOAc:Hexanes) to give 5-chloro-N-[3-methyl-5-(1,3-thiazol-5-yl)phenyl]pyrimidin-2-amine (2.95 g, 73%) as a white solid. MS ESI: [M+H]+ m/z 303. 1H NMR (500 MHz, CDCl3) δ 8.75 (s, 1H), 8.37 (s, 2H), 8.08 (s, 1H), 7.71 (s, 1H), 7.33 (s, 1H), 7.09 (s, 1H), 2.40 (s, 3H). rhSYK activity=++.

Provenance & Evidence