Cesium carbonate → {3,5-Dichloro-4-[4-(6-methylpyrimidin-4-ylamino)thiazolo[5,4-c]pyridin-2-yl]-phenyl}-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of [3,5-dichloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-phenyl]-carbamic acid tert-butyl ester (0.30 g, 0.697 mmol), 6-methylpyrimidin-4-ylamine (0.073 g, 0.77 mmol), XantPhos (0.040 g, 0.0696 mmol) and Cs2CO3 (0.454 g, 1.39 mmol) in dioxane (10 mL) was degassed with a stream of argon. Pd2(dba)3 (0.032 g, 0.035 mmol) was added and the reaction mixture was heated at 85° C. for 18 hours. After cooling to room temperature, the crude reaction mixture was filtered through Celite® washing with EtOAc and the filtrate was concentrated under reduced pressure. The resultant residue was purified by column chromatography on silica gel eluting with 0-30% EtOAc in petroleum ether to afford the title compound as a yellow solid (0.238 g, 68% yield). LCMS (Method D): RT=3.14 min, m/z: 503 [M+H+].

Provenance & Evidence