461-98-3

Usage

Chemical Properties

Crystalline Solid

InChI:InChI=1/C6H9N3/c1-4-3-6(7)9-5(2)8-4/h3H,1-2H3,(H2,7,8,9)

Upstream product

• 67-56-1 methanol 
• 823-94-9 2,4,6-trimethyl-s-triazine 
• 4472-45-1 4-chloro-2,6-dimethylpyrimidine 
• 75-05-8 acetonitrile 
• 108260-15-7 2-(iodomethyl)-6-methyl-4-pyrimidinylamine 
• 1118-61-2 3-Aminocrotononitrile 
• 7664-41-7 ammonia 
• 108-24-7 acetic anhydride 
• 143-37-3 acetamidine 
• 142-96-1 dibutyl ether 
• 109-75-1 but-3-enenitrile 
• 124-42-5 acetamidine hydrochloride 
• 70807-22-6 3-hydroxycrotononitrile sodium salt 

Downstream Products

• 33721-00-5 N-(2,6-dimethylpyrimidin-4-yl)acetamide 
• 79513-89-6 N-(4-chloro-phenyl)-N'-(2,6-dimethyl-pyrimidin-4-yl)-urea 
• 100376-08-7 4-chloro-benzoic acid-(2,6-dimethyl-pyrimidin-4-ylamide) 
• 61736-26-3 4-methyl-7-phenyl-pyrrolo[1,2-a]pyrimidin-2-ylamine 
• 667907-86-0 N-benzenesulfonyl-N-(2,6-dimethyl-pyrimidin-4-yl)-benzenesulfonamide 
• 108236-13-1 [4-(2,6-dimethyl-pyrimidin-4-ylsulfamoyl)-phenyl]-carbamic acid ethyl ester 
• 847700-01-0 4-nitro-benzenesulfonic acid-(2,6-dimethyl-pyrimidin-4-ylamide) 
• 667908-37-4 N-(2,6-dimethyl-pyrimidin-4-yl)-4-nitro-N-(4-nitro-benzensulfonyl)-benzenesulfonamide 
• 515-64-0 Sulfasomidin 
• 112860-70-5 4-acetylamino-N-(4-acetylamino-benzenesulfonyl)-N-(2,6-dimethyl-pyrimidin-4-yl)-benzenesulfonamide 
• 124813-74-7 C₁₃H₁₂N₂O₅S₂*C₆H₉N₃ 
• 109773-85-5 5,7-Dimethyl-3-phenylimino-3H-1,2,4-thiadiazolo<4,3-c>pyrimidine 
• 124813-70-3 C₁₄H₁₆N₄O₃S*C₆H₉N₃ 
• 124232-33-3 methyl (Z)-2-benzoylamino-3-(2,6-dimethyl-4-pyrimidinyl)aminopropenoate 

Relevant academic research and scientific papers

Temperature controlled condensation of nitriles: Efficient and convenient synthesis of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines in one system

A series of β-enaminonitriles, 4-aminopyrimidines and 4-amidinopyrimidines were synthesized by condensation of organonitriles in one system. A wide variety of compounds were obtained in good to excellent yields by simply controlling the reaction temperature. The base-induced transformation process is easy for production. The scope and versatility of the method have been successfully demonstrated with 72 examples. The flexible and diversified characteristics of nitriles were introduced based on electronic effect, steric effect, position of substituted groups and intermolecular hydrogen bonding. An updated reaction mechanism is proposed based on the study of the stoichiometric reaction conditions at variable temperature, and on the investigation of products with cis-trans configuration transformation.

Synthesis and characterization of the coordination polymer [(THF)K(μ-OPri)2Al(μ-OPri)2]n

Reaction of [Al(OPri)3] with K(OPri), in 1:1 molar ratio in refluxing anhydrous tetrahydrofuran yields a polymeric complex [(THF)K(μ-OPri)2Al(μ-OPri)2]n. The complex is characterized by spectroscopic studies and single crystal X-raydiffraction analysis.

Hydrophosphination using [GeCl{N(SiMe3)2}3] as a pre-catalyst

Transformations catalyzed by germanium are scarce, with examples mainly limited to widely catalyzed processes such as polymerisation of lactide and hydroboration of carbonyls. Reported is the first example of hydrophosphination using a germanium pre-catalyst, yielding anti-Markovnikov products when diphenylphosphine is reacted with styrenes or internal alkynes at room temperature. This journal is

Aryl Insertion vs Aryl-Aryl Coupling in C,C-Chelated Organoborates: The "missing Link" of Tetraarylborate Photochemistry

The photoreactivity of 9-borafluorene-based, C,C-chelated organoborates was investigated. Unlike the related tetraarylborates, the charge-transfer transitions imparted by the biphenyl chelate lead to selective insertion of one aryl substituent into the endocyclic B-C bond of the 9-borafluorene moiety, resulting in the formation of boratanorcaradienes. This photoreaction likely proceeds according to a Zimmerman rearrangement, which is analogous to one of the initially proposed mechanisms for tetraarylborates and provides additional insight into these long-debated photochemical reactions.

Organoselenium and DMAP co-catalysis: Regioselective synthesis of medium-sized halolactones and bromooxepanes from unactivated alkenes

A catalytic system consisting of bis(4-methoxyphenyl)selenide and 4-(dimethylamino)pyridine (DMAP) has been developed for the regioselective synthesis of medium-sized bromo/iodo lactones and bromooxepanes possessing high transannular strain. 77Se NMR, mass spectrometry and theoretical studies reveal that the reaction proceeds via a quaternary selenium intermediate.

Lewis acid-catalyzed synthesis of 4-aminopyrimidines: A scalable industrial process

Pyrimidine synthesis starting from acrylonitrile has been known since the 1960s. The new Lewis acid-catalyzed condensation reaction allows the synthesis of 4-aminopyrimidines starting from the easily accessible chemical acrylonitrile without the need for carcinogenic chemicals and costly derivatization in up to 90% yield. The method is versatile and applicable for industrial-scale synthesis of biologically relevant substances such as vitamin B1 and trimethoprim.

Syntheses, structures, and electronic properties of the branched oligogermanes (Ph3Ge)3GeH and (Ph3Ge) 3GeX (X = Cl, Br, I)

The branched oligogermanium hydride (Ph3Ge)3GeH was synthesized via a hydrogermolysis reaction from GeH4 and Ph 3GeNMe2 and was converted to the halide series of compounds (Ph3Ge)3GeX (X = Cl, Br, I) upon reaction with [Ph3C][PF6] in CH2X2 solvent (X = Cl, Br, I). These species were fully characterized by NMR (1H and 13C) and UV/visible spectroscopy, cyclic voltammetry, and elemental analysis. In addition, (Ph3Ge)3GeH was analyzed by 73Ge NMR spectroscopy and exhibits two resonances at δ -56 and -311 ppm. A Ge-H coupling constant of 191 Hz was observed in the proton-coupled 73Ge NMR spectrum of (Ph3Ge)3GeH. The X-ray crystal structures of (Ph3Ge)3GeH and (Ph 3Ge)3GeX (X = Cl, Br, I) were obtained and represent the first examples of branched oligogermane hydrides or halides to be characterized in this fashion. The Ge-Ge bond distances in (Ph3Ge)3GeH are short (average value 2.4310(5) A), while those in the halide compounds (Ph3Ge)3GeX are similar to one another and range from 2.4626(7) to 2.4699(5) A. The UV/visible and cyclic voltammetry data for these species have been correlated with DFT computations, and excellent agreement was found between the experimental and theoretical data.

Synthesis and evaluation of 2-(2,6-dihalophenyl)-3-pyrimidinyl-1,3-thiazolidin-4-one analogues as anti-HIV-1 agents

A series of 2-(2,6-dihalophenyl)-3-(substituted pyrimidinyl)-1,3-thiazolidin-4-ones were designed on the prediction of quantitative structure-activity relationship (QSAR) studies, synthesized, and evaluated as HIV-1 reverse transcriptase inhibitors. Our attempts in correlating the identified molecular surface features related properties for modeling the HIV-1 RT inhibitory activity resulted in some statistically significant QSAR models with good predictive ability. The results showed that compounds 4m and 4n were highly active in inhibiting HIV-1 replication with EC50 values in the range of 22-28 nM in MT-4 as well as in CEM cells with selectivity indexes of >10,000. The derived models collectively suggest that the compounds should be compact without bulky substitution on its peripheries for better HIV-1 RT inhibitory activity. These models also indicate a preference for hydrophobic compounds to obtain good HIV-1 RT inhibitory activity.

RhCl3-catalyzed hydroboration of alkenyl nitriles

RhCl3-promoted hydroboration-oxidation reactions of representative alkenyl nitriles have been carried out. Carbanion of acetonitrile is formed from the carbon-carbon heterolytic bond breaking in allyl cyanide during hydroboration. An unexpected process-trimerization of carbanion of acetonitrile has lead to the formation of 4-amino-2,6-dimethylpyrimidine.

N-fluorotriazinium fluorinating agents

Novel N-fluorotriazinium electrophilic fluorinating agents have the Formula I: wherein three A moieties are independently CR, where each R is, independently, hydrogen, halogen, hydroxyl, (primary, secondary or tertiary) amino, amino, cyano, perfluorothio, hydroxysulfonyl, halosulfonyl, hydrocarbyloxysulfonyl, or a carbon-containing substituent selected from the group consisting of optionally substituted hydrocarbyl, hydrocarbyloxy, hydrocarbyloxycarbonyl, and hydrocarbylthio groups, and at least one R is neither hydrogen nor halogen; two A moieties are independently Z, where each Z is independently nitrogen or a quaternary nitrogen atom and Y is a counterion or group of counterions which are inert to chemical attack by fluorine, or adjacent triazinium moieties are linked by a common R substituent to provide an oligomer or polymer. Preferably the compounds are 1,3,5-triazinium compound in which all R are the same, optionally perfluorinated, alkyl or alkoxy groups; Z1 and Z2 are both nitrogen and Y? is triflate. Compounds of Formula I are especially useful in fluorinating carbanionic species or activated aromatic compounds.