Potassium Phosphate, Tribasic → Ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a 40 mL vial charged with 5-chloro-3-(6-phenylpyridin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine (Int-18e, 582 mg, 1.0 mmol), Pd(dppf)Cl2 (82 mg, 0.1 mmol), K3PO4 (636 mg, 3.0 mmol), and ethyl 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate (441 mg, 1.5 mmol) was added dioxane (20 mL including 1 mL water). The mixture was thoroughly degassed by alternately evacuating the flask under vacuum, then placing it under an argon atmosphere numerous times. The reaction was then heated to 90° C. and stirred overnight. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (30 mL) and filtered through celite. The solvent was removed under reduced pressure and the residue was purified with column (silica gel, 0-30% ethyl acetate in hexane) gave ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-methylcyclohex-3-enecarboxylate (Int-18f) (630 mg). HPLC-MS tR=2.89 min (UV254 nm); mass calculated for formula C39H55N5O4Si2 713.4, observed LCMS m/z 714.4 (M+H).

Provenance & Evidence