Potassium Phosphate, Tribasic → 5-chloro-3-(5-fluoro-4-(methylthio)pyrimidin-2-yl)-1-trityl-1H-pyrazolo[3,4-b]pyridine

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Reaction Conditions

Reaction Steps

A mixture of 2-chloro-5-fluoro-4-methylsulfanyl-pyrimidine (0.26 g, 1.44 mmol) and 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-trityl-pyrazolo[3,4-b]pyridine, 33, (0.75 g, 1.44 mmol) and K3PO4 (0.96 g, 4.53 mmol) in water (1.5 mL) and 2-Me-THF (7.5 mL) was degassed with nitrogen bubbling for 15 min. Then, X-Phos (0.07 g, 0.14 mmol) and Pd2(dba)3 (0.03 g, 0.04 mmol) was added and the vessel was sealed and heated to 125° C. with microwave irradiation for 30 min. After cooling to room temperature, water was added and the mixture was extracted and with ether and 2-Me-THF. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Flash chromatography (SiO2, 0-100% EtOAc-hexanes, gradient elution) provided 230 mg of the desired product which was used without further purification: LC/MS Gradient 10-90%, 0.1% formic 5 min, C18/ACN, RT=3.46 min (M+H) 538.01.

Provenance & Evidence