Antidiabetische wirkstoffe. III. 4,5,6-Trisubstituierte 2-(4-toluidino)pyrimidine

The condensation of 4-tolyiguanidine ( 1 ) with the β-kiketones 2a-b yields the 2-(4-toluidino)pyrimidines 3a-b .     

Antimykotische wirkstoffe. XIX. 4,6-Disubstituierte 2-(cyanamino)pyrimidine

The reaction of city dicyandiamide ( 1 ) with β-diketones 2a-c leads to 2-(cyanoamino)pyrimidines 3a-c. Structure type 3 is supported by spectroscopic data, while at the same time a 1-cyano-2-imino structure ( 4 ) is excluded. Compound 3a exhibits fungistatic and nematicidal activity.     

Potentiell tumorhemmende wirkstoffe. IX. 4,5,6-trialkylierte 2-methoxy- und 2-(methylthio)pyrimidine

The interaction of O-methylisourea sulfate ( 1a ) or S-methyl-isothiourea sulfate ( 1b ), respectively, with 3-methyl-2,4-pentanedi-one ( 2a ) yields 2-methoxy-( 3a )and 2-methylthio-4,5,6-trimethyl-pyrimidine ( 3b ). The 5-ethylpyrimidines ( 3c and 3d ) obtained by the analogous reactions with 3-ethyl-2,4-pentanedione ( 2b ), in contact with air exhibit a tendency to cleave off the 5-ethyl group and give 4,6-dimethyl-2-methoxypyrimidine ( 4a ) and 4,6-dimethyl-2-(melhylthio)pyrimidine ( 4b ).     

Antimykotische wirkstoffe. XV. . Die halogensubstitution bei phenoxy-1,3,5-triazinen

Through the nucleophilic substitution of one chlorine atom in 2,4-dichloro-6-diethylamino-1,3,5-triazine ( 1 ) by halophenols ( 2a-f ) the 2-chloro-4-diethylamino-6-halophenoxy-1,3,5-triazines ( 3a-f ) are accessible. Structure 3 comprises representatives exhibiting antimycotic activity.     

Antimykotische wirkstoffe. VIII. Aufbau von dehydro-N-mannich-basen durch piperidin- und piperazinring

The three component reactions comprising the interaction of cyanamide ( 1 ) and s-triazine ( 2 ) with a secondary amine ( 5 ) leads to dehydro-N-Mannich bases ( 6 ). Of this compound class, 6a, b, and c exhibit antimycolic activity.     

Analgetika. VIII. Fluoralkylsubstituierte 2-(äthylamino)pyrimidine

2-Ethylaminopyrimidines ( 3 ) substituted by fluoroalkyl groups may be obtained through the reaction of ethylguanidine ( 1 ) with appropriately substituted (J-diketones ( 2 ). Within compound class 3 , representatives occur exhibiting analgesic, antiinflammatory, and antifungal activity.     

Antimykotische wirkstoffe. XXI. Aliphatisch und alicyclisch substituierte chlor-diallylamino-1l,3,5-triazine

By nucleophilic substitution of one chlorine atom in 2,4-dichloro-6-(diallylamino)-1,3,5-triazine(1) by amines 2a-g, the alkylamino and cycloalkylamino-chloro-(diallylamino)-1,3,5-triazines 3a-g are obtained. Typical spectroscopic singals of structure type 3 are the ir-band at 800 cm^μ caused by the 1,3,5-triazine ring, the four ¹ nmr signals between 4.1-6.1 ppm to be assigned to the allyl groups, and the mass s[ectrpscopic peak of the ring cation m/e 158. Representatives of compound class 3 exhibit marked antimycotic, trichomonacidal, and herbicidal activity.     

Conformational analysis of 4-(2′-furyl)-2-(methylamino)pyrimidine

Conformational transformations of the title compound 1 were studied using high-resolution ¹H-nmr techniques, semi-empirical PM3 calculations and molecular dynamics. The unfused furan-pyrimidine ring system of 1 predominantly exists in an s-trans conformation in solution and the considerable sp² character of the C2?amino bond results in the hindered rotation which is observed on the nmr time scale.     

Antibakterielle wirkstoffe. IX . Die aminomethinylierung im system des 3-methyi-1-(4-nitrophenyl)-2-pyrazolin-5-ons

The aminomethinylation of 3-methyl-l-(4-nitrophenyl)2-pyrazolin-5-one ( 2 ) by means of s-triazine ( 1 ) leads to the aminomethinylation product 4 and the C-rubazoic acid type 5 . The mass spectra supporting the structures obtained exhibit the pyrazolo[4,3-d]isoxazolylium ion 6 (m/e 245), p-benzoquinonemonoiminyl cation (m/e 106), and methyleneaminophenyl cation (m/e 104) as characteristic fragments of 4 .     

Synthesis,polarography and herbicidal activity of quaternary salts of 2-(4-pyridyl)-1,3,5-triazines, 5-(4-pyridyl)pyrimidine, 2-(4-pyridyl)pyrimidine and related compounds

2-(4-Pyridyl)-1,3,5-triazine, 2-(4-pyridyl)-4-methyl-1,3,5-triazine, 2-(4-pyridyl)-4,6-dimethyl-1,3,5-triazine and 2-(4-pyridyl)pyrimidine have been prepared by modification of established triazine and pyrimidine syntheses. These compounds and some of their relatives have been converted to quaternary pyridinium salts. The polarographic reduction potentials of the salts in aqueous solution are pH dependent. The activity of the salts as post-emergent herbicides is reported.     

Synthesis of C-4 substituted pyrimidine nucleoside analogs. Preparation of several 4-(2-oxoalkylidene)-2(1H)-pyrimidinone ribonucleosides

A series of 4-(1-alkynyl)-2(1H)-pyrimidinone ribonucleosides were synthesized from the Pd-catalyzed coupling of terminal alkynes to the 4-chloropyrimidin-2-one ribonucleoside ( 2 ). These compounds were hydrated, using three different methods, to afford the 4-(2-oxoalkylidene)-2(1H)-pyrimidinones. The 4-enol-pyrimidin-2-one structure of the title compounds offers functional groups with the potential for Watson-Crick hydrogen bonding.     

Concise, flexible syntheses of 4-(4-imidazolyl)pyrimidine cyclin-dependent kinase 2 (CDK2) inhibitors

A flexible six-step synthesis of potential cyclin-dependent kinase 2 (CDK2) inhibitors is reported. The synthesis involves the condensation between 3-chloro-4,4-dimethoxy-2-butanone and amidines, which provides acetyl-imidazoles and late stage palladium-catalyzed N-arylation to give the target pyrimidine derivatives.     

Tautomeric equilibrium of 1-β-D-ribofuranosyl-2-keto-4-(n-methoxyamino)pyrimidine

The 1-β-D-ribofuranosides of 2-keto-4-(N-methoxyamino)pyrimidine, 2-keto-4-(N-methyl-N-methoxyamino)pyrimidine, and 2-keto-3-methyl-4-(N-methoxyamino)pyrimidine were synthesized, and their pK_a values were determined by spectrophotometry. The pK_a values of the compounds are evidence that the tautomeric equilibrium between the oxime and hydroxyamine forms of 1-β-D-ribofuranosyl-2-keto-4-(N-methoxyamino)pyrimidine in aqueous solutions is shifted to favor the oxime form (K_T?25).     

Pyridine and pyrimidine ring syntheses from 4-(4-morpholino)-3-pentenone and from ethyl 3-(4-morpholino)-2-butenoate

3-Substituted 2(1H)-pyridones are produced from reaction of 4-(4-morpholino)-3-pentenone 1 with each of the following carbon acids: cyanoacetamide, malononitrile, cyanothioacetamide, acetylacetamide, benzoyl-acetonitrile. Reaction of ethyl 3-(4-morpholino)-2-butenoate 2 with cyanoacetamide gives the corresponding hydroxypyridone. Pyrimidines are formed by reaction of 1 and of 2 with benzamidine and with S-benzylthio-urea; in the last case, the eliminated morpholine displaces the benzylthio group to give the final product.     

Preparation and characterization of symmetrical bis[4-chloro-2-pyrimidyl] dichalcogenide (S, Se, Te) and unsymmetrical 4-chloro-2-(arylchalcogenyl) pyrimidine: X-ray crystal structure of 4-chloro-2-(phenylselanyl) pyrimidine and 2-(p-tolylselanyl)-4-chloropyrimidine

Synthesis of a novel class of multinucleate pyrimidine chalcogen (S/Se/Te) derivatives has been successfully attempted for the first time by the selective substitution of chlorine at the C-2 position of 2,4-dichloropyrimidine with nucleophilic dichalcogenide anion E₂²⁻ (E = S, Se, Te) to afford bis[4-chloro-2-pyrimidyl] dichalcogenide. The highly electrophilic nature of 2,4-dichloropyrimidine compared to aryl chlorides has been further exploited to prepare a variety of 4-chloro-2-(arylchalcogenyl) pyrimidine compounds by substituting the chlorine exclusively at the C-2 position of 2,4-dichloropyrimidine with a variety of chalcogen bearing aryl anions ArE⁻ (Ar = phenyl, 1-naphthyl, p-tolyl, 4,6-dimethyl-2-pyrimidyl, 2-pyridyl, 4-methyl-2-pyridyl). All the newly prepared symmetrical and unsymmetrical pyrimidyl chalcogen compounds have been thoroughly characterized with the help of various spectroscopic techniques viz., NMR (¹H, ¹³C, ⁷⁷Se), FT-IR and mass spectrometry (in representative cases). The crystal structures of 4-chloro-2-(phenylselanyl) pyrimidine and 2-(p-tolylselanyl)-4-chloropyrimidine have been determined by X-ray crystallography.     

Anhydro base of 4-(3-indolyl)pyrimidine

The reaction of 4-(3-indolyl)pyrimidine methiodide with alkali gives a stable anhydro base, which reacts under mild conditions with methyl iodide to give 1-methyl-4-(1-methyl-3-indolyl)pyrimidinium iodide. On the basis of the calculated molecular diagrams of both compounds it was concluded that they have high reactivities. The reaction of the anhydro base with an aqueous methanol solution of KOH, concentrated NH₄OH, hydrazine hydrate, and a mixture of malonic acid dinitrile with triethylamine leads to 3-acetylindole, 4-(3-indolyl)pyrimidine, 3(5)-(3-indolyl)pyrazole, and 2-amino-3-cyano-6-(3-indolyl)pyridine, respectively. 1-Methyl-4-(1-methyl-3-indolyl)pyrimidinium iodide under the same conditions gives similar compounds that contain a methyl group attached to the indole nitrogen atom. The structures of the synthesized compounds were confirmed by their IR, UV, PMR, and mass spectra.See [1] for our preliminary communication.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 212–218, February, 1982.