1850-98-2Relevant academic research and scientific papers
Desulfonative photoredox alkylation of: N -heteroaryl sulfones-an acid-free approach for substituted heteroarene synthesis
Wang, Zheng-Jun,Zheng, Shuai,Matsui, Jennifer K.,Lu, Zhipeng,Molander, Gary A.
, p. 4389 - 4393 (2019/04/29)
Minisci-type alkylation of electron-deficient heteroarenes has been a pivotal technique for medicinal chemists in the synthesis of drug-like molecules. However, such transformations usually require harsh conditions (e.g., strong acids, stoichiometric amou
'Green' synthesis of 2-substituted 6-hydroxy-[3H]-pyrimidin-4-ones and 4,6-dichloropyrimidines: Improved strategies and mechanistic study
Opitz, Andreas,Sulger, Werner,Daltrozzo, Ewald,Koch, Rainer
, p. 814 - 824 (2015/05/20)
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.
Compounds as syk kinase inhibitors
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Paragraph 0816; 0817, (2013/03/26)
The present invention relates to a compound of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by inhibition of Syk kinase.
4-AMINO-PYRIMIDINE DERIVATIVES
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Page/Page column 76, (2009/07/25)
4-Amino-pyrimidine derivatives of Formula (I), wherein the meaning of the different substituents are those indicated in the description. These compounds are useful as histamine H4 receptor antagonists.
