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: 163.001
  • Purity: ≥95%
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Catalog Number R019712
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 />
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