Pyridine → HCID 46840938, compound

Participants

Reaction Steps

Ethyl 7-(4-cyanophenyl)-5-methyl-2-[(trifluoroacetyl)amino]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (45 mg, 107 μmol) and 3-(trifluoromethyl)phenylboronic acid (61 mg, 321 μmol, 3 eq.) were initially charged together with anhydrous copper(II) acetate (58 mg, 321 μmol, 3 eq.) and molecular sieve (0.1 g, 4 Å) and, under an atmosphere of argon protective gas, suspended in abs. dichloromethane (3 ml). Abs. pyridine (69 μl, 856 μmol, 8 eq.) and triethylamine (45 μl, 321 μmol, 3 eq.) were then added. After 12 h of stirring, more 3-(trifluoromethyl)phenylboronic acid (20 mg, 107 μmol, 1 eq.), anhydrous copper(II) acetate (19 mg, 321 μmol, 1 eq.) and pyridine (35 μl, 428 μmol, 4 eq.) were added, and the mixture was stirred for a further 24 h. The mixture was then filtered through kieselguhr, the filter residue was washed with dichloromethan and methanol and the filtrate concentrated under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 10 μm, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (10.3 mg, 17% of theory).

Provenance & Evidence