4,6-Dichloro-2-methylpyrimidine

For research use only. Not for therapeutic Use.

  • CAT Number: R019712
  • CAS Number: 1780-26-3
  • Molecular Formula: C5H4Cl2N2
  • Molecular Weight: 163.00
  • Purity: ≥95%
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4,6-Dichloro-2-methylpyrimidine (Cat No.: R019712) is a heterocyclic aromatic compound consisting of a pyrimidine ring substituted with chlorine atoms at the 4 and 6 positions and a methyl group at the 2 position. This compound is a valuable intermediate in organic synthesis, particularly in the pharmaceutical and agrochemical industries. Its reactive chlorine atoms allow for selective nucleophilic substitution reactions, making it useful in the preparation of various biologically active molecules, such as kinase inhibitors, antiviral agents, and herbicides. It offers versatility for structure–activity relationship studies.


CAS Number 1780-26-3
Synonyms

2-Methyl-4,6-dichloropyrimidine; Pyrimidine, 4,6-dichloro-2-methyl-

Molecular Formula C5H4Cl2N2
Purity ≥95%
Storage Store at -20C
IUPAC Name 4,6-dichloro-2-methylpyrimidine
InChI InChI=1S/C5H4Cl2N2/c1-3-8-4(6)2-5(7)9-3/h2H,1H3
InChIKey FIMUTBLUWQGTIJ-UHFFFAOYSA-N
SMILES CC1=NC(=CC(=N1)Cl)Cl
Reference

[1]. Su, Bin; Li, Hui; Cai, Meng Shen; and Li, Zhong Jun, &quot;On the Mechanism of Condensation between 5-Amino-4, 6-dichloro- 2-methylpyrimidine and 1-Acetyl-2-imidazolin-2-one&quot;.<br />
Abstract The condensation reaction between 5-amino-4, 6-dichloro-2-methylpyrimidine and 1-acetyl-2-imidazolin-2-one using POCl3 as solvent gave 4, 6-dichloro-2-methyl-5-(1-acetyl-tetra-hydro-imidazo-2-ylidene)- aminopyrimidine predominantly and 4, 6-dichloro-2-methyl-5-{1-[1-(2-oxo-tetrahydro-imidazolyl)]-acetyene}- aminopyrimidine as by-product. No 4, 6-dichloro-2-methyl-5-(1-acetyl-2-imidazolin-2-yl)-aminopyrimidine was found. The result indicated an esterifi- cation-addition-elimination mechanism.<br />
2002. Chemistry Faculty Publications. 440. https://engagedscholarship.csuohio.edu/scichem_facpub/440 Volume.13 Issue.3.<br />
<br />
[2]. Synthesis and Process Research of 4,6-Dichloro-2-methylpyrimidine<br />
CHEN Lei-xiang,DENG Sheng-song,GUAN Qiu-xiang,GU Lei-ming(School of Medical Engineering,Hefei University of Technology,Hefei 230009,China)<br />
4,6-Dichloro-2-methylpyrimidine is an important intermediate of synthetic anticancer drug dasatinib.4,6-dichloro-2-methylpyrimidine was synthesized from acetamidine hydrochloride and dimethyl malonate via the cyclization and chlorination with phosphorus oxychloride.The optimal conditions of synthesis of 4,6-dihydroxy-2-methylpyrimidine were investigated by orthogonal test.They were: n(acetamidine hydrochloride)/n(sodium methoxide)=1∶3.4,in methanol at 20℃ for 4h,the yield of 4,6-dihydroxy-2-methylpyrimidine was 85.76%.The optimal conditions of chlorination with phosphorus oxychloride were investigated by orthogonal test.They were: n(N,N-diethyl-Benzenamine)/n(4,6-dihydroxy-2-methylpyrimidine)=2∶1,in phosphorus oxychloride at 105℃ for 4h,the yield of 4,6-dichloro-2-methylpyrimidine was 69.55%,the yield of two-steps was 59.65%.<br />
https://en.cnki.com.cn/Article_en/CJFDTotal-AHHG201204014.htm<br />
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[3]. Researches on Pyrimidines: Certain Derivatives of 2-Methylpyrimidine<br />
Henry R. Henze, William J. Clegg, and Charles W. Smart<br />
The Journal of Organic Chemistry 1952 17 (10), 1320-1327 DOI: 10.1021/jo50010a007<br />
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[3]. Etude th&eacute;orique structurale et spectroscopique infrarouge et Raman de 4, 6-Dichloro-2-Methylpyrimidine<br />
Author Medjani, M Brihi, O Hamdouni, N Boudjada, A Meinnel, J<br />
Dans le cadre de ce travail nous pr&eacute;sentons les r&eacute;sultats des calculs pour la d&eacute;termination de la conformation mol&eacute;culaire dans le produit 4,6-dichloro-2-methylpyrimidine obtenu &agrave; partir du calcul th&eacute;orique bas&eacute; sur la th&eacute;orie de la fonctionnelle de la densit&eacute; DFT. Ces r&eacute;sultats de calcul, pour d&eacute;terminer la conformation mol&eacute;culaire de la mol&eacute;cule isol&eacute;e est obtenu en s&lsquo;aidant de la cha&icirc;ne de programmes GAUSSIAN en utilisant la fonctionnelles d&lsquo;&eacute;change-corr&eacute;lation B3LYP et des bases suffisamment &eacute;tendues adapt&eacute;es aux produits organiques pour conduire &agrave; des &eacute;valuations tr&egrave;s pr&eacute;cises pour les longueurs et angles de liaison, tr&egrave;s proches des r&eacute;sultats exp&eacute;rimentaux r&eacute;pertori&eacute;s dans la litt&eacute;rature. Les modes internes mol&eacute;culaires sont calcul&eacute;s en utilisant comme dans l&lsquo;optimisation g&eacute;om&eacute;trique la fonctionnelle B3LYP et les jeux de bases 6-311 et DGTZVP. Nous terminons l&#39;expos&eacute; de ce travail par la comparaison des r&eacute;sultats de calcul th&eacute;orique des modes de vibrations obtenus &agrave; partir de ces deux fonctionnelles avec les fr&eacute;quences exp&eacute;rimentales de la spectroscopie infra &ndash; rouge et raman<br />
http://hdl.handle.net/123456789/135816

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