Sodium hydride → Methyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetate

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Reaction Steps

The compound methyl 2-(4-hydroxyphenyl)acetate (330 mg, 0.2 mmol) was dissolved in dry DMF (3 mL) and NaH (80 mg, 60% in oil, 0.2 mmol) was added and the mixture was stirred at room temperature for 5 min. Then, 5-chloro-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (430 mg, 0.1 mmol) was added and the resulting mixture was heated up to 130° C. with microwave and stirred for 30 min. After cooling to room temperature, NH4Cl (aq) was added to quench the reaction and extracted with EtOAc (50 mL×3). The combined organics were washed with water and brine and dried over Na2SO4. After concentration, the residue was purified with column (silica gel, 20% EtOAc/Hexane) gave the product, methyl 2-(4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetate, (490 mg) as clear oil. HPLC-MS tR=2.77 min (UV254 nm); mass calculated for formula C27H42N4O5Si2 558.3, observed LCMS m/z 559.3 (M+H).

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