Sodium Carbonate → HCID 71547537, compound

Participants

Reaction Conditions

Reaction Steps

To solution of 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6,7-dihydrothieno[3,2-d]pyrimidine 5,5-dioxide (50 mg, 0.16 mmol), in 2.0 mL of DME/H2O (4/1, v/v) was added 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (59.7 mg, 0.20 mmol) and Na2CO3 (52.3 mg, 0.49 mmol). The mixture was degassed twice, and then catalytic amount of Pd(dppf)Cl2 (10 mg, 0.013 mmol) was added. The mixture was heated to 80° C. and stirred for 3 h under nitrogen. The resulting mixture was then cooled and diluted with EtOAc and H2O the aqueous layer was extracted with ethyl acetate and the combined organic layers were combined, washed by brine, dried over anhydrous Na2SO4, filtered, and then evaporated to give the crude which was purified by column chromatography on silica gel (eluent: CH2Cl2/ethyl acetate=30/1˜1/1) to provide 1-cyclopropyl-3-[4-[4-[(3S)-3-methylmorpholin-4-yl]-5,5-dioxo-6,7-dihydrothieno[3,2-d]pyrimidin-2-yl]phenyl]urea as a white solid, (30.0 mg, 41%).

Provenance & Evidence