Sodium Carbonate → Methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)-2-methoxybenzoate

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Reaction Steps

To a solution of 5-chloro-N-(3,4-dimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (155 mg, 0.48 mmol) and methyl 2-methoxy-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)benzoate (180 mg, 0.44 mmol) in 10 mL of 1,4-dioxane and 1 mL of water was added Na2CO3 (140 mg, 1.32 mmol) followed by Pd(PPh3)4 (26 mg) under nitrogen with stirring. The mixture was refluxed for 15 hours under nitrogen. After cooled, the solvent was evaporated by rotary evaporation. The residue was purified by column chromatography on silica gel eluting with (petroleum ether:EtOAc=1:1) to give methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzamido)-2-methoxybenzoate (160 mg, 64%) as solid. LC-MS: 572 [M+H]+, tR=1.62 min.

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