Sodium hydride → HCID 86686668, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanol (820 mg, 1.21 mmol) in DCM (10 mL) was added TEA (0.337 mL, 2.42 mmol), followed by MsCl (0.104 mL, 1.33 mmol) at 0° C. and stirred for 1 h. The reaction mixture was concentrated, and then dissolved in EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated to afford a pale yellow oil. This oil was dissolved in DMF (10 mL). MeSO2NH2 (1.5 eq) was added, followed by NaH (4.0 eq). The resulting reaction mixture was heated at 90° C. for 2 d. The reaction mixture was diluted with EtOAc, neutralized with NH4Cl, washed with H2O and brine, dried over Na2SO4, and concentrated. The crude product was purified by a SiO2 column (0-10% MeOH/DCM, Rf=0.65 in 10% MeOH/DCM) to afford N-((4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)-1-hydroxycyclohexyl)methyl)methanesulfonamide as a brownish oil (594 mg). HPLC-MS TR=2.86 min (UV 254 nm, 10 min method); mass calculated for formula C37H56N6O5SSi2 752.4, observed LCMS m/z 753.1 (M+H).

Provenance & Evidence