3740-82-7

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Benzyl-4,6-dichloropyrimidine serves as a valuable building block in the synthesis of pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with potential therapeutic or pesticidal properties.
Used in Material Science:
This chemical compound may also be utilized in the development of new materials, thanks to its distinct chemical characteristics. It can contribute to the creation of advanced materials with specific properties for various applications.
Used in Research Applications:
2-Benzyl-4,6-dichloropyrimidine is a useful tool in research settings, where its properties can be explored and harnessed for the advancement of scientific knowledge and the development of innovative technologies.

InChI:InChI=1/C11H8Cl2N2/c12-9-7-10(13)15-11(14-9)6-8-4-2-1-3-5-8/h1-5,7H,6H2

Upstream product

• 3740-83-8 2-benzyl-1H-pyrimidine-4,6-dione 

Downstream Products

• 796095-93-7 3-(2-benzyl-6-chloro-pyrimidin-4-ylamino)-propionic acid methyl ester 

Relevant academic research and scientific papers

'Green' synthesis of 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones and 4,6-dichloropyrimidines: Improved strategies and mechanistic study

An improved route to 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones 4 and to 2-substituted 4,6-dichloropyrimidines 5 is reported. Without using highly toxic reactants, compounds 4 can be prepared conveniently in a one pot synthesis on a one mol scale with average yields up to 80%. 4,6-Dichloropyrimidines 5, which are usually prepared in small quantities, are synthesized with average yields of 80%, using up to 80g of starting material. The mechanism of the chlorination of 4 is investigated computationally for the first time. The results suggest that the chlorination with phosphoryl chloride occurs in an alternating phosphorylation-chlorination manner (pathway 1) which is preferred over a sequence which starts with two phosphorylations. The investigated 4,6-dichloropyrimidines described herein form strong complexes with dichlorophosphoric acid but weak complexes with hydrochloric acid (generated during workup). These latter complexes explain the necessity of using aqueous sodium carbonate during the working up. In order to prevent possible formation of pyrimidinium salts between intermediates or the final dichloropyrimidines and unreacted hydroxypyrimidone, the latter could be deactivated with a strong acid such as dichlorophosphoric acid, thus allowing chlorination but prohibiting salt formation. Because of its general applicability to all nitrogen heterocycle chlorinations with phosphoryl chloride, the proposed route to dichloropyrimidines without solvent or side products, using less toxic reactants, is of general synthetic interest.