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Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 120-46-7 1,3-diphenylpropanedione 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 59807-21-5 2-(methylsulfanyl)-4,6-diphenylpyrimidine 
• 100-52-7 benzaldehyde 
• 874-90-8 4-methoxybenzonitrile 
• 98-86-2 acetophenone 
• 1529527-71-6 C₂₃H₂₂N₂O 
• 19293-52-8 1,3-diphenyl-propanediyldiamine 
• 98-85-1 1-Phenylethanol 
• 22265-37-8 4-methoxybenzamidine 
• 100-51-6 benzyl alcohol 

Relevant academic research and scientific papers

Acceptorless Dehydrogenative Synthesis of Pyrimidines from Alcohols and Amidines Catalyzed by Supported Platinum Nanoparticles

A one-pot, acceptorless dehydrogenative method, using a carbon-supported Pt catalyst (Pt/C) along with KOtBu, has been developed for the synthesis of 2,4,6-trisubstituted pyrimidines from secondary and primary alcohols, and amidines. The reaction takes place efficiently using a wide range of substrate scopes (32 examples with isolated yields up to 92%). The Pt/C catalyst that promotes this process is reusable and has a higher turnover number (TON) than those employed in previously reported methods. The results of mechanistic studies suggest that the process takes place through a pathway that begins with Pt-catalyzed acceptorless dehydrogenation of the alcohol substrate, which is followed by sequential condensation, cyclization, and dehydrogenation. Measurements of the turnover frequency combined with the results of density functional theory calculations on different metal surfaces suggest that the adsorption energy of H on the Pt surface is optimal for the acceptorless dehydrogenation process, which causes the higher catalytic activity of Pt over those of other metals.

A sustainable multicomponent pyrimidine synthesis

Since alcohols are accessible from indigestible biomass (lignocellulose), the development of novel preferentially catalytic reactions in which alcohols are converted into important classes of fine chemicals is a central topic of sustainable synthesis. Multicomponent reactions are especially attractive in organic chemistry as they allow the synthesis of large libraries of diversely functionalized products in a short time when run in a combinatorial fashion. Herein, we report a novel, regioselective, iridium-catalyzed multicomponent synthesis of pyrimidines from amidines and up to three (different) alcohols. This reaction proceeds via a sequence of condensation and dehydrogenation steps which give rise to selective C-C and C-N bond formations. While the condensation steps deoxygenate the alcohol components, the dehydrogenations lead to aromatization. Two equiv of hydrogen and water are liberated in the course of the reactions. PN5P-Ir-pincer complexes, recently developed in our laboratory, catalyze this sustainable multicomponent process most efficiently. A total of 38 different pyrimidines were synthesized in isolated yields of up to 93%. Strong points of the new protocol are its regioselectivity and thus the immediate access to pyrimidines that are highly and unsymmetrically decorated with alkyl or aryl substituents. The combination of this novel protocol with established methods for converting alcohols to nitriles now allows to selectively assemble pyrimidines from four alcohol building blocks and 2 equiv of ammonia.

Efficient and benign one-pot conversion of n-tosyl-1,4,5,6- tetrahydropyrimidines to pyrimidines via tandem β-elimination and aromatization

An efficient, mild, benign, and practical method for one-pot conversion of N-tosyl-1,4,5,6-tetrahydropyrimidines into pyrimidines is discussed in detail. In this method, N-tosyl-1,4,5,6-tetrahydropyrimidines are first prepared via N-tosylation of tetrahyd

A direct oxidative route for the synthesis of pyrimidines using heteropolyacids

Pyrimidines are synthesized via a direct oxidative one-pot, three-component, reaction between 1,3-diketone, benzaldehydes, and ammonium acetate in the presence of catalytic amounts of Keggin-type heteropolyacids under refluxing conditions in good yields.

Microwave-assisted simple, one-pot, four-component synthesis of 2,4,6-triarylpyrimidines under solvent-free conditions

2,4,6-Triarylpyrimidines are synthesized via a simple, one-pot, four-component reaction between aryl methyl ketones, benzaldehydes, aromatic nitriles, and hydroxylamine under microwave irradiation and solvent-free conditions in good to excellent yields.

Pyrimidine-core extended π-systems: General synthesis and interesting fluorescent properties

We have developed a simple but powerful synthetic strategy that permits the assembly of π-systems onto a pyrimidine core in a programmable and diversity-oriented format. The nucleophilic addition of ArLi to 2-methylthiopyrimidine, followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation, resulted in the production of 4-aryl-2-methylthiopyrimidines. The iterative reaction sequence then gave 4,6-diaryl-2-methylthiopyrimidines. The resulting adduct was further allowed to react with ArMgBr under the catalytic influence of NiCl2(dppe) to afford 2,4,6-triarylpyrimidines. By following this synthetic scheme, interesting pyrimidine-core π-systems were rapidly constructed in a programmable fashion. The successful discovery of a number of interesting fluorescent materials and properties (e.g., solvatofluorochromism) speaks well for the potential of our platform strategy in the development of functional organic materials. Copyright

A convenient method for the preparation of highly substituted 1101 pyrimidines: Synthesis of tri- and tetra-subsituted pyrimidines from 1,3-dicarbonyl compounds and N,N,N′-tris-(trimethylsilyl)amidines

A modification of the Pinner pyrimidine synthesis has been developed that utilizes trimethylsilyl amidines and results in greatly improved yield of highly substituted pyrimidines.

Reaction of α,α-dibromo oxime ethers with Grignard reagents: Alkylative annulation providing a pyrimidine core

A convergent synthesis of a pyrimidine core has been achieved. Treatment of α,α-dibromo oxime ethers, which are easily derived from the corresponding esters, with a variety of Grignard reagents provides trisubstituted pyrimidines in good yields. This new

A NOVEL CONVENIENT ONE STEP PYRIMIDINE SYNTHESIS

A new method for the preparation of pyrimidines by condensation of β-dicarbonyl compounds, ammonium salts and carbonyl containing substances has been developed.