Water → HCID 71548605, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-5-methyl-4-[(3S)-3-methylmorpholin-4-yl]-5,7-dihydrothieno[3,4-d]pyrimidine 6,6-dioxide (100 mg, 0.3147 mmol) in DME/H2O (2 mL, 4/1, v/v) were added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (114.1 mg, 0.37 mmol) and sodium carbonate (100.1 mg, 0.94 mmol) The reaction was degassed twice and a catalytic amount of Pd(dppf)Cl2 (10 mg, 0.013 mmol) was added to the suspension. The mixture was heated at 80° C. for 3 h under a nitrogen atmosphere. The resulting mixture was cooled and H2O was added. The mixture was extracted with ethyl acetate and the combined organic layers washed with brine, dried over anhydrous Na2SO4, filtered, and then evaporated. The residue was purified by column chromatography on silica gel (eluent: CH2Cl2/ethyl acetate=20/1˜5/1) and preparative HPLC to provide the product as a white solid (30.0 mg, 21%).

Provenance & Evidence