Uses
6-Phenyl-2-thiouracil is a thyreostatic (thyroid hormone) agent that may be used as a reference material in thyreostatic drug separation and detection technologies such as capillary electrophoresis, HPLC, or gas chromatography.
Synthesis
To a solution of ethyl benzoylacetate (2 g, 10.41 mmol) in ethanol (15 mL) was added sodium ethoxide (7 mL, 18.7 mmol) and compound (CAS:17356-08-0) (1.18 g, 15.61 mmol). The reaction mixture was stirred under reflux conditions overnight. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in water, the pH was adjusted to 3 with acid and extracted with ethyl acetate (3 x 20 mL). The organic phases were combined, washed with brine and dried over anhydrous sodium sulfate. The crude product was purified by fast column chromatography using dichloromethane/methanol (2.5%) as eluent to afford 2-mercapto-6-phenyl-4-hydroxypyrimidine (500 mg, 2.44 mmol) as a white solid in 24% yield.
References
[1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 1999, vol. 54, # 6, p. 788 - 798
[2] Synthetic Communications, 2002, vol. 32, # 6, p. 851 - 855
[3] Patent: WO2016/30534, 2016, A1. Location in patent: Page/Page column 109
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 745 - 759
[5] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 203
