2,6-Lutidine → HCID 66628259, compound

Participants

Reaction Steps

Under an atmosphere of argon protective gas, (rac)-7-(4-cyanophenyl)-2-methoxy-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (50 mg, 171 μmol) was stirred in abs. dichloromethane (7 ml) with molecular sieve (0.5 g, 4 Å) for 1 h. 3-(Trifluoromethyl)phenylboronic acid (97 mg, 513 μmol, 3 eq.), anhydrous copper(II) acetate (93 mg, 513 μmol, 3 eq.), abs. pyridine (8 ml) and triethylamine (72 μl, 513 μmol, 3 eq.) were then added, and the mixture was stirred at RT for 48 h. More anhydrous copper(II) acetate (31 mg, 171 μmol, 1 eq.) and 2,6-lutidine (60 μl, 513 μmol, 3 eq.) were then added, and the mixture was stirred under an atmosphere of dry air at RT for a further 7 d. The reaction mixture was then concentrated to dryness. The residue was suspended in ethyl acetate (10 ml) and filtered. The filtrate was washed with water (5 ml) and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Reprosil C18 column, 10 μm; mobile phase: acetonitrile/water+0.1% TFA 10:90→90:10). The brown solid obtained in this manner was decolorized by filtration through a small silica gel cartridge using a mobile phase mixture of cyclohexane and ethyl acetate (2:1) and then lyophilized. The product was obtained as a solid (10.8 mg, 15% of theory).

Provenance & Evidence