1,4-Dioxane → 5,6,7,8-Tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidin-4(3H)-one

Participants

Reaction Conditions

Reaction Steps

Into a 20 ml microwave tube was combined 5,6,7,8-Tetrahydro-3H-pyrido[4,3-d]pyrimidin-4-one (0.280 g, 0.00183 mol), 2-chloro-5-methylpyridine (0.47 g, 0.0037 mol), 1,4-dioxane (2.5 mL, 0.032 mol) N,N-diisopropylethylamine (0.64 mL, 0.0037 mol) and N,N-dimethylacetamide (0.5 mL, 0.005 mol). The mixture was heated via microwave at 150° C. for 4 hours. The mixture was reduced in vacuo and taken up in chloroform:IPA (3:1) (50 ml). The organic was washed with sodium bicarbonate and brine (1×50 ml), dried over sodium sulfate, and reduced in vacuo. The mixture was purified by flash chromatography on silica gel using a methylene chloride:methanol (0-10%) gradient. The combined pure fractions were reduced in vacuo to yield a bright yellow solid (0.215 g, 47.9%).

Provenance & Evidence