4-HYDROXY-6-(TRIFLUOROMETHYL)PYRIMIDINE-2-THIOL synthesis
- Product Name:4-HYDROXY-6-(TRIFLUOROMETHYL)PYRIMIDINE-2-THIOL
- CAS Number:368-54-7
- Molecular formula:C5H3F3N2OS
- Molecular Weight:196.15
Yield: 90%
Reaction Conditions:
for 4 h;Reflux;
Steps:
3.2.1. Synthesis of 6-Substituent-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1a-1f)
General procedure: All of the thiouracil derivatives (R1 = CH3, C2H5, n-Pr, cyc-Pr, CHF2, CF3) were prepared asfollowed. To a 1000mLthree-neck flask equipped with a magnetic stirrer, a thermometer, and a droppingfunnel, 500 mL of methanol and 59.4 g (1.1 mol) of solid sodium methoxide were added, and the mixturewas then stirred at room temperature. After 0.5 h, 0.5 mol (93.0 g) of ethyl 4,4,4-triuoro-3-oxobutanoateand 0.6 mol of thiourea were added to the flask, and the mixture was heated to reflux for about 4 h.Finally, a 2 M HCl aqueous solution was added to the flask until the reaction mixture was neutralized.The resultant solid was separated by filtration, then washed with water, and finally dried in a desiccatorto produce 88.3 g of intermediate 1b as a white solid at a yield of 90%; melting point: 247.5-248.2 C;1H NMR (500 MHz, DMSO-d6) δ 13.37 (br, 1H), 12.78 (s, 1H), 6.34 (s, 1H).
References:
Hao, Shulin;Cai, Zengfei;Cao, Yangyang;Du, Xiaohua [Molecules,2020,vol. 25,# 15,art. no. 3379]
