Methyl iodide → 2,3-Dimethyl-6-phenyl-5-(prop-2-yn-1-yl)pyrimidin-4(3H)-one

Participants

Reaction Steps

A mixture of 0.76 g (3.4 mmol) of 2-methyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone, 0.72 g (5.2 mmol) of anhydrous potassium carbonate, 0.32 mL (5.1 mmol) of methyl iodide and 20 mL of methyl ethyl ketone was heated at reflux for 6 h. The mixture was cooled, diluted with 40 mL of water and extracted with two 60 mL portions of ethyl acetate. The ethyl acetate extracts were dried and rotovaped to leave 0.75 g of crude product. This material was purified by flash chromatography on silica gel to afford 0.71 g of 2,3-dimethyl-6-phenyl-5-propargyl-4(3H)-pyrimidinone as a white solid, mp 142°-144° C., 1H-NMR (CDCl3) δ 2.10(3H,t,J=4), 2.60(3H,s), 3.40(2H,d,J=4), 3.60(3H,s), 7.45(3H,m), 7.65(2H,m); IR(nujol) 3200, 1650 cm-1.

Provenance & Evidence