Methyl formate → 5-(2-Methyl-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

Participants

Reaction Steps

To the suspension of NaH, 60% (1.3 eq, 130 mg) in 600 μl of dry 1,2-dimethoxyethane, under argon atmosphere was carefully added, via syringe, a solution of 3-(2-Methyl-pyrimidin-5-yl)-propionic acid methyl ester (450 mg, 2.5 mmol, 1 eq) and methyl formate (4 eq, 616 μl) in 3 ml of dry 1,2-dimethoxyethane. The resulting suspension was stirred overnight (16 hours) at room temperature. In the reaction mixture was then added 3 ml of dry diethyl ether. The resulting precipitate was collected; it was washed with 3 ml of diethyl ether and dried. It was dissolved in 4 ml of absolute ethanol, thiourea (1.5 eq, 285 mg) was added and the reaction mixture was stirred at reflux under argon atmosphere for 8 hours. Solvent was then evaporated, the rest was dissolved in 3 ml of water and pH value of the solution was adjusted to 4.5-5 using 3N HCl water solution. The resulting precipitate was collected, it was washed with water and dried to afford 5-(2-Methyl-pyrimidin-5-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (210 mg, yield=35.9%, purity=95%) in form of white powder. MS: [M+H]+=235.17 1H NMR (300 MHz; DMSO-d6) δ/ppm 2.54 (s, 3H), 3.50 (s, 2H), 7.48 (s, 1H), 8.55 (s, 2H), 12.38 (br.s., 2H)

Provenance & Evidence