反应详情

To a suspension of NaH, 60% dispersion on mineral oil (1.3 eq, 320 mg, 60%) in 1.5 ml of dry 1,2-dimethoxyethane under argon atmosphere was added a solution of 3-(2-methoxy-pyridin-4-yl)-propionic acid methyl ester (1.2 g, 6.14 mmol, 1 eq) and methyl formate (2 eq, 760 μl) in 8 ml of dry 1,2-dimethoxyethane. The sealed mixture was stirred at room temperature for 16 hours (overnight). Solvent from the mixture was then evaporated. In the rest was added 15 ml of diethyl ether and using ultrasound bath the precipitate was formed. Mother liquor was removed and in the rest was triturated once more with diethyl ether. The precipitate was dried and was dissolved in 10 ml of absolute ethanol, thiourea (1.5 eq, 700 mg) and triethylamine (1.1 eq, 936 μl) were added and the resulting mixture was heated at 90° C. (temperature on display of heating device) for 2 hours. The solvent was evaporated and the rest was dissolved in 10 ml of water. pH of the solution was adjusted to 6-7 and the formed precipitate was collected by filtration and was dried to 5-(2-methoxy-pyridin-4-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (900 mg, yield=58.7%, purity=95%). MS: [M+H]+=250.15 1H NMR (300 MHz; DMSO-d6) δ/ppm 3.51 (s, 2H), 3.81 (s, 3H), 6.65 (s, 1H), 6.85 (dd, J=5.42 Hz, J=1.03 Hz 1H), 7.42 (s, 1H), 8.03 (d, J=5.42 Hz, 1H), 12.02-12.76 (m, 2H)

1. customSolvent from the mixture was then evaporated
2. additionIn the rest was added 15 ml of diethyl ether
3. customwas formed
4. customMother liquor was removed and in the rest
5. customwas triturated once more with diethyl ether
6. customThe precipitate was dried
7. dissolutionwas dissolved in 10 ml of absolute ethanol
8. temperaturethe resulting mixture was heated at 90° C.
9. temperature(temperature on display of heating device) for 2 hours
10. customThe solvent was evaporated
11. dissolutionthe rest was dissolved in 10 ml of water
12. filtrationthe formed precipitate was collected by filtration