56741-94-7Relevant articles and documents
An efficient microwave assisted synthesis of N′-aryl/(alkyl)-substituted N-(4-hydroxy-6-phenylpyrimidin-2-yl)guanidines: Scope and limitations
Machicao, Paulo A.,Burt, Scott R.,Christensen, Ryan K.,Lohner, Nathan B.,Singleton,Peterson, Matt A.
, p. 2318 - 2321 (2017)
Treatment of N-[(4-hydroxy-6-phenyl)pyrimidin-2-yl]cyanamide with 1° alkyl or arylamines in isopropyl alcohol for only 10?min at 110–120?°C under microwave conditions gave the corresponding N′-alkyl(aryl)guanidine derivatives in excellent yields (65–84%). Isolated yields were greatest when >1.0?equiv. of amines were employed, but excellent results were also obtained when aryl and alkylamines were reacted with a more atom-economical loading (1.0?equiv.; 70% and 72% ave. yields, respectively). Arylamines with either highly electron withdrawing substituents (e.g. CO2H) or pi-deficient heterocycles (e.g. variously substituted aminopyridines) did not work well under these conditions, and reaction with ureas and/or amino acids did not give detectable products. Work-up was exceedingly simple, and involved simple collection and washing of product on a sintered glass funnel. Products were obtained in analytically pure form and required approximately 1?h to prepare, start to finish.
High-Performance Liquid Chromatographic Determination of 5-Halopyrimidinone Interferon Inducers
Wynalda, M. A.,Fitzpatrick, F. A.
, p. 1931 - 1934 (1980)
High-performance liquid chromatography with microparticulate, bonded, reversed-phase columns separates closely related 5-halopyrimidinones that are interferon inducers.A method was developed to a quantitate serum levels of 2-amino-5-bromo-6-phenyl-4(3H)-pyrimidinone, an important analogue of this new series.The method is, with minor modifications, suitable to measure other 5-halophenylpyrimidinone analoques.Results show that the quantitation of serum levels as low as 2 μg mL-1 is possible with ultraviolet detection at 235 nm.Protein precipitation and extraction prior to chromatography improve the daily sample throughput by removing interfering peaks with capacity factors greater than 45.Preliminary results indicate a species-dependent variation in the half-lives of elimination of the free compound after its administration, orally, to experimental animals.Rats clear the drug with a half-life of 4.5 h; cats clear the drug with half-lives ranging from 10 to 18 h depending on the dose administered.The differences in metabolic clearance may be relevant to observed toxicity differences between these species.
Controlling Keto-Enol Tautomerism of Ureidopyrimidinone to Generate a Single-Quadruple AADD-DDAA Dimeric Array
Ding, Qinwen,Dong, Zeyuan,Fan, Zengming,Mao, Shizhong,Qi, Shuaiwei,Zhang, Chenyang,Zhang, Jing
supporting information, p. 7305 - 7309 (2020/10/05)
Units of ureidopyrimidinone (UPy) which dimerize via strong quadruple hydrogen bonding are widely used for the construction of supramolecular systems. This self-complementary system exists in the tautomerism equilibrium of 4[1H]-pyrimidinone dimer and pyrimidin-4-ol dimer, making generated supramolecular assembly systems essentially complicated. In this contribution, a rational but simple design concept is described for preorganizing the self-complementary quadruple hydrogen bonding of UPy via supramolecular strategy into a single-quadruple DDAA-AADD dimeric array. With this concept, the designed UPy derivatives form only 4[1H]-pyrimidinone dimer with a ketone configuration via intermolecular hydrogen-bonding interactions, both in the solid state as well as in solution, as is evident from single-crystal X-ray diffraction and 1H NMR spectroscopy. The single DDAA-AADD dimeric array provides defined noncovalent driving forces that can be used to generate constitutionally clear supramolecular structures that are vitally important in the fields of supramolecular chemistry and materials.
Synthesis of 6-arylisocytosines and their potential for hydrogen bonding interactions
Patel, Alpa,Lewis, William,Searle, Mark S.,Stevens, Malcolm F.G.,Moody, Christopher J.
supporting information, p. 7339 - 7343 (2015/08/24)
Abstract The synthesis of a number of 6-arylisocytosines, including linked bis-isocytosines, from the reaction of guanidine with β-ketoesters is described. The compounds were investigated for their ability to form hydrogen-bonded structural networks, and for their potential interactions with the telomeric quadruplex forming sequence AGGG(TTAGGG)3.
