179329-51-2

Upstream product

• 1670-14-0 benzamidine monohydrochloride 
• 1122594-14-2 1-(4-bromophenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 
• 618-39-3 benzamidin 
• 1122-91-4 4-bromo-benzaldehyde 
• 121-44-8 triethylamine 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 99-90-1 para-bromoacetophenone 
• 22731-70-0 1-(4-bromophenyl)prop-2-en-1-one 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 4592-94-3 3-(4-bromophenyl)-3-oxopropanenitrile 
• 10342-83-3 4'-Bromopropiophenone 
• 1450619-00-7 4-(4-bromophenyl)-6-trichloromethyl-2-phenyl-1,6-dihydropyrimidine 

Downstream Products

• 160522-98-5 4-[4-(4,5-Dihydro-1H-imidazol-2-yl)-phenyl]-2-phenyl-pyrimidine 

Relevant academic research and scientific papers

Construction of a Pyrimidine Framework through [3 + 2 + 1] Annulation of Amidines, Ketones, and N, N-Dimethylaminoethanol as One Carbon Donor

An efficient, facile, and eco-friendly synthesis of pyrimidine derivatives has been developed. It involves a [3 + 2 + 1] three-component annulation of amidines, ketones, and one carbon source. N,N-Dimethylaminoethanol is oxidized through C(sp3)-H activation to provide the carbon donor. One C-C and two C-N bonds are formed during the oxidative annulation process. The reaction shows good tolerance to many important functional groups in air, making this methodology a highly versatile alternative, and significant improvement to the existing methods for structuring a pyrimidine framework, especially 4-aliphatic pyrimidines.

I2-Catalyzed Aerobic α,β-Dehydrogenation and Deamination of Tertiary Alkylamines: Highly Selective Synthesis of Polysubstituted Pyrimidines via Hidden Acyclic Enamines

A novel and efficient entrance to the pyrimidine skeleton has been presented via the α,β-dehydrogenation and deamination of tertiary alkylamines. This I2-catalyzed dehydrogenative multicomponent procedure utilizes simple aldehydes to trap the hidden enami

Synthesis method of pyrimidine compound containing alkyl and aryl

The invention discloses a synthesis method of a pyrimidine compound containing alkyl and aryl, and belongs to the technical field of organic synthesis. Key points of the technical scheme of the invention are as follows: the synthesis method of the pyrimidine compound containing alkyl and aryl comprises the following specific steps: dissolving an aldehyde compound, an amidine hydrochloride compoundand a tertiary aliphatic amine compound in a solvent, adding an iodine reagent and an oxidant, and carrying out a reaction process at 110-150 DEG C to prepare the pyrimidine compound containing alkyland aryl as a target product. The synthesis process is simple and efficient, the pyrimidine compound is directly prepared by one step through a one-pot cascade reaction without transition metal catalysis so that resource waste and environmental pollution caused by use of various reagents in multi-step reaction, purification treatment of reaction intermediates in each step and the like are avoided, the synthesis process is convenient to operate, the raw materials are simple, the reaction conditions are mild, the substrate application range is wide, and meanwhile, alkyl substituents are ingeniously introduced by taking the tertiary fatty amine compound as the raw material.

Direct synthesis of 2,4,5-trisubstituted imidazoles and di/tri-substituted pyrimidines via cycloadditions of α,β-unsaturated ketones/aldehydes and N′-hydroxyl imidamides

An efficient route for the synthesis of 5-acetylimidazoles and di/trisubstituted pyrimidines via iron-catalyzed cross-dehydrogenative coupling (CDC), with excellent tolerance and yields, has been developed. In this report, α,β-unsaturated aldehydes/ketones and N′-hydroxyl imidamides undergo [3+2] and [3+3] cycloadditions in two processes, involving iron-mediated Michael reaction, Robinson Annulation and 1,5-electrocyclization.

Preparation method of polysubstituted pyrimidine

The invention belongs to the field of chemical synthesis, and particularly relates to a preparation method of polysubstituted pyrimidine. The method comprises the following step that amidine hydrochloride and a propiophenone compound react in the presence of an iron source compound, 1,10-phenanthroline and tetramethyl piperidine nitric oxide to obtain polysubstituted pyrimidine, wherein propiophenone or a propiophenone derivative is adopted as the propiophenone compound. According to the method, polysubstituted pyrimidine can be generated through a reaction by taking the propiophenone compound and amidine hydrochloride as reacting raw materials under combined promotion of the iron source compound, 1,10-phenanthroline and the tetramethyl piperidine nitric oxide; a strong alkaline or strong acidic environment is not needed, the reaction conditions are simple and mild, and the yield of polysubstituted pyrimidine is high. Experiment results show that the maximum yield of polysubstituted pyrimidine prepared through the method can reach 93% or above.

Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines

An efficient method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C-H bond functionalization. Control experiments were performed to gain deep understanding of the mechanism, and the reactions are likely to proceed through a designed TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.

A new convenient synthetic approach to diarylpyrimidines

A new synthetic method in pyrimidine chemistry has been developed. 2,2,2-Trichloroethylideneacetophenones, easily available from chloral and acetophenones, reacted with benzamidines to provide novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydr

Chemoselective Reduction of α-Cyano Carbonyl Compounds: Application to the Preparation of Heterocycles

β-Aminoacrylates are reactive intermediates that are useful building blocks in synthesis. General methods for their preparation typically afford α and β disubstitution patterns or β only. Molecules with only α-substituents (β-hydrogen) are much less well-known. A chemoselective reductive tautomerization of α-cyanoacetates, using DIBAL-H, has been developed to access these valuable synthons. α,β-Unsaturated cyanoacetates and α-cyanoketones can, also, be selectively reduced via this methodology. A series of heterocycles were prepared using these β-enamino carbonyl compounds.

Cu-Catalyzed [3 + 3] Annulation for the Synthesis of Pyrimidines via β-C(sp3)-H Functionalization of Saturated Ketones

A novel, efficient, and facile approach for the synthesis of structurally important pyrimidines has been successfully developed by Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones. This method provides a new protocol for the synthesis of pyrimidines by a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization via direct β-C(sp3)-H functionalization of saturated ketones followed by annulation with amidines.

A new improved method for the synthesis of 2,4-diarylpyrimidines starting from 2,2,2-trichloroethylideneacetophenones

An advantageous new approach to 2,4-diarylpyrimidines has been developed. 2,2,2-Trichloroethylideneacetophenones reacted with benzamidines leading to novel 2,6-diaryl-6-hydroxy-4-trichloromethyl-1,4,5,6-tetrahydropyrimidines in near quantitative yields. These compounds were efficiently dehydrated to obtain previously unknown 2,4-diaryl-6-trichloromethyl-1,6-dihydropyrimidines, which were able to undergo aromatisation via chloroform elimination to give 2,4-diarylpyrimidines in high yields. A main improvement of this procedure lies in circumventing the oxidative dehydrogenation of dihydropyrimidine intermediates. This preparative process has also been adapted to a one-pot protocol.