HCID 13028015, compound → HCID 22617850, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 7-chloro-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-pyrazolo[1,5-a]pyrimidine (0.26 g, 8.69×10−4 mol) in 2 mL N-methylpyrrolidine, and add N-(2-aminoethyl)-2-(4-methoxyphenyl)acetamide (0.75 g, 3.6 mmol). Heat to 80° C. overnight under N2. Partition between EtOAc (50 mL) and H2O (50 mL), then separate layers and wash EtOAC layer successively with 0.1 N NaOH (25 mL), H2O (25 mL), and brine. Pool aqueous layers and extract with EtOAc (25 mL). Pool EtOAc layers, dry over Na2SO4, filter and concentrate to yellow oil. Chromatograph on silica gel eluting with EtOAc and evaporate to obtain 0.30 g of N-(3-(2,4,6-trimethylphenyl)-2,5-dirnethyl-pyrazolo[1,5-a]pyrimidin-7yl)-2-(4-methoxyphenyl)acetamide as a clear pale yellow oil. LCMS=472.3 (MH+); 470.2 (M−). 1H-NMR (CDCl3): 7.10 (d, 2H, J=10.2 Hz); 6.39 (s, 2H); 6.81 (d, 2H, J=10.2 Hz); 6.46 (t, 1H, J=6.0 Hz); 6.16 (t, 1H, J=6.0 Hz); 5.79 (s, 1H); 3.76 (s, 3H); 3.45-3.50 (m, 6H); 2.38 (s, 3H); 2.30 (s, 3H); 2.20 (s, 3H); 2.02 (s, 6H).

Provenance & Evidence