4-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methyl-6-((5-methylpyridin-2-yl)ethynyl)pyrimidine → 4-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methyl-6-(2-(5-methylpyridin-2-yl)ethyl)pyrimidine

Participants

Reaction Steps

A slurry of 4-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methyl-6-((5-methylpyridin-2-yl)ethynyl)pyrimidine (1-4, 80 mg, 0.188 mmol, 1.0 eq.) in a mixture of dichloromethane (3 ml) and ethanol (3 ml) was treated with palladium on carbon (60 mg, 0.564 mmol, 3.0 eq.) under a hydrogen balloon for 4 hours. The reaction mixture was filtered through C-lite, and the C-lite was washed with dichloromethane (3×100 mL). The filtrate was concentrated and purified by reverse phase liquid chromatography (H2OCH3CN gradient w/ 0.1% TFA present) to afford 4-(5-(3,4-dimethoxybenzyl)-1H-1,2,4-triazol-1-yl)-2-methyl-6-(2-(5-methylpyridin-2-yl)ethyl)pyrimidine (1-5). 1H NMR (500 MHz, CDCl3) δ 8.36 (s, 1H), 7.95 (s, 1H), 7.57 (s, 1H), 7.38 (dd, 1H, J=7.9 Hz, 2.3 Hz), 7.04 (d, 1H, J=7.9 Hz), 6.86 (m, 2H), 6.79 (d, 1H, J=8.1 Hz), 4.75 (s, 2H), 3.84 (s, 3H), 3.83 (s, 3H), 3.22 (s, 4H), 2.75 (s, 3H), 2.69 (s, 3H), 2.30 (s, 3H) HRMS m/z (M+H) 431.2185 found, 431.2190 required.

Provenance & Evidence