Sodium Carbonate → Methyl 3-(7-(3-(trifluoromethyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate

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Reaction Conditions

Reaction Steps

To a stirred solution of 5-chloro-N-(3-(trifluoromethyl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (330 mg, 1 mmol), methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (314 mg, 1.2 mmol) and Na2CO3 (498 mg, 4.7 mmol) in 2 mL of water and 20 mL of dioxane was added Pd(PPh3)4 (93 mg, 0.075 mmol) in one portion at room temperature under nitrogen. Then the mixture was stirred at 95° C. for 16 hours under nitrogen. The solvent was evaporated at 40° C. at reduced pressure and the residue was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (4:1)) to give methyl 3-(7-(3-(trifluoromethyl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)benzoate (365 mg, 84.8%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 9.18 (s, 1H), 8.93 (s, 1H), 8.74 (d, 1H, J=7.8 Hz), 8.61 (s, 1H), 8.21 (brs, 2H), 7.94 (d, 1H, J=7.8 Hz), 7.65-7.60 (m, 2H), 7.48-7.46 (m, 1H), 4.01 (s, 3H). LC-MS: 431 [M+H]+, 429 [M−H]−, tR=1.92 min. HPLC: 95.92% at 214 nm, 97.01% at 254 nm, tR=5.14 min.

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