Methylthiouracil synthesis
- Product Name:Methylthiouracil
- CAS Number:56-04-2
- Molecular formula:C5H6N2OS
- Molecular Weight:142.18
141-97-9
17356-08-0
56-04-2
Sodium metal (30 mmol) was added to methanol (10 mL) and after complete dissolution, thiourea (10 mmol) and ethyl acetoacetate (10 mmol) were added sequentially. The reaction mixture was heated to reflux for 7 hours. After completion of the reaction, methanol was removed by distillation under reduced pressure and the residue was dissolved in an appropriate amount of water and the pH was adjusted to neutral with acetic acid. The precipitate was collected by filtration to give the pale yellow crystalline product methylthiouracil (1.26 g, 90% yield). The product was characterized as follows: melting point 275-277°C; 1H NMR (δ, ppm): 2.09 (s, 3H, 6-CH3), 5.52 (s, 1H, CH-pyrimidine), 11.98 [b.s, 2H, (NH)2]; 13C NMR (δ, ppm): 17.88, 103.38, 151.91, 160.32, 175.83. 175.83. Elemental analysis results (C5H6N2OS) calculated values: C, 42.24; H, 4.25; N, 19.70; S, 22.55; measured values: C, 42.24; H, 4.25; N, 19.70; S, 22.55.
Yield:56-04-2 91%
Reaction Conditions:
with potassium hydroxide in ethanol at 80; for 5 h;
Steps:
1 Step 1:
To a vial was added ethyl 3-oxobutanoate (1 g, 8.0 mmol, 1 eq.), thiourea (0.6, 8.0 mmol, 1 eq.) and KOH (0.4 g, 8.0 mmol, 1 eq.) in ethanol (6 ml). The reaction mixture was stirred at 80° C. for 5 h. Ethanol was removed under reduced pressure to one third of its original volume, the reaction mixture was then poured into water and neutralized with 2 N HCl. The resulting mixture was left stirring overnight at rt. A precipitate formed and was filtered by vacuum filtration to provide the desired product 6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1.0 g, 7.033 mmol, 91%) as white solid. ESI-MS: 143.2 [M+H]+.
References:
Purdue Research Foundation;Watts, Val J.;van Rijn, Richard M.;Flaherty, Daniel P.;Kaur, Jatinder US2019/23688, 2019, A1 Location in patent:Paragraph 0152
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