With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.1820-81-1, name is 5-Chlorouracil, molecular formula is C4H3ClN2O2, molecular weight is 146.53, as common compound, the synthetic route is as follows.category: pyrimidines
General procedure: A mixture of 5-fluorouracil (50.5 mg, 0.39 mmol), pyridine (0.60 mL), and HMDS (1.2 mL) in a20-mL Schlenk tube was refluxed (oil bath temp., 140 C) for ca. 30 min to give a clear solution of 2a. All the volatiles were then removed under reduced pressure (ca. 1mmHg) to give a clear syrup, which was dissolved in MeCN (3.0 mL). To this were added 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1) (151.5 mg, 0.30 mmol) and6 (5.8 mg, 15 mumol), and the mixture was stirred under reflux (oil bath temp., 80 C) for6 h. The reaction mass was cooled to rt and EtOAc (2 mL) was added to it, followed by saturated NaHCO3 solution (2 mL). After the mixture was stirred at 0 C for 15min, EtOAc (30 mL) and saturated NaHCO3 solution (20 mL) were added to it. The organic phase was separated and the aqueous phase was back-extracted with EtOAc (3 x30 mL). The combined organic layer was dried over Na2SO4 and evaporated to afforda foamy white crude material, which was crystallized from EtOAc (10 mL) and hexane(20 mL) as a white solid (139.2 mg). The mother liquor was purified by column chromatography (Silica Gel 60, 8 g, EtOAc:hexane = 30:70 35:65) to afford the titlecompound 3a (15.6 mg). The combined yield was 90% (155 mg). 1H and 13C NMR spectra were consistent with the reported ones.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,1820-81-1, 5-Chlorouracil, and friends who are interested can also refer to it.
Reference:
Article; Basu, Nabamita; Oyama, Kin-ichi; Tsukamoto, Masaki; Tetrahedron Letters; vol. 58; 20; (2017); p. 1921 – 1924;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia