Reference of 1004-40-6 ,Some common heterocyclic compound, 1004-40-6, molecular formula is C4H5N3OS, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
To a solution of 1-(bromomethyl)-4-tert-butylbenzene (2.00 ml, 9.00 mmol) in 10 mL of EtOH was added a solution of 6-amino-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (2.00 g, 12.0 mmol) in EtOH (35.0 ml, 9.00 mmol), water (4.00 ml, 9.00 mmol), and 3.45 M aqueous NaOH solution (4.00 ml, 13.0 mmol). The whole was heated at 50 C. After 16 h, LCMS showed mainly the product. The reaction was cooled down to rt and concentrated. Water was added until all solids had precipitated out of the solution. The solids were filtered off with an aid of water. White solid was obtained and was purified further by performing a column chromatography using 70:30 DCM:(90:10:1 DCM:MeOH:NH4OH). The product, 2-(4-tert-butylbenzylthio)-6-aminopyrimidin-4(3H)-one was obtained as a white solid (1.8 g, 69% yield). LCMS (ESI) Calcd for C15H19N3OS: [M]+ = 289. Found [M+H]+ = 290. The carbon shift data supported the structure of 6-amino-2-(4-tert-butylbenzylthio)pyrimidin-4(1H)-one. However, line-broadening in the 1D proton and carbon data suggested the double-bond is probably moving between the two nitrogens. Thus, 6-amino-2-(4-tert-butylbenzylthio)pyrimidin-4(1H)-one and 2-(4-tert-butylbenzylthio)-6-aminopyrimidin-4(3H)-one were in equilibrium in DMSO-d6. Proton and carbon chemical shift assignments for 2-(4-tert-butylbenzylthio)-6-aminopyrimidin-4(3H)-one in DMSO-d6 were shown below.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1004-40-6, its application will become more common.
Reference:
Article; Nguyen, Hanh Nho; Bregman, Howie; Buchanan, John L.; Du, Bingfan; Feric, Elma; Huang, Liyue; Li, Xingwen; Ligutti, Joseph; Liu, Dong; Malmberg, Annika B.; Matson, David J.; McDermott, Jeff S.; Patel, Vinod F.; Wilenkin, Ben; Zou, Anruo; McDonough, Stefan I.; Dimauro, Erin F.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 2; (2012); p. 1055 – 1060;,
Pyrimidine | C4H4N2 – PubChem,
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