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CS-W001157 4
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4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

  • CAS No. 115093-90-8

  • Cat. No. CS-W005653
  • Purity≥98%
  • MDL No.MFCD09999173

*For research and further manufacturing use only, not for direct human use.

4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine|CS-W005653

Structure of 115093-90-8

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General Information

  • CAS No. 115093-90-8
  • Cat. No. CS-W005653
  • Purity ≥98%
  • MDL No. MFCD09999173
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃Cl₂N₃
  • Molecular Weight 188.01
  • Synonym(s) 7H-pyrrolo[2,3-d]pyrimidine, 4,5-dichloro-
  • SMILES ClC1=CNC2=NC=NC(Cl)=C21

Description

4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine features a rigid heterocyclic core with two chlorine substituents at electron-deficient positions, enabling efficient coupling in cross-coupling reactions. This bench-stable compound integrates readily into purine-based scaffolds, offering enhanced reactivity for medicinal chemistry applications.

Application

4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine serves as a versatile building block for purine-derived scaffolds, enabling efficient construction of heterocyclic frameworks through palladium-catalyzed cross-coupling reactions. Its dual chloro substituents provide orthogonal reactivity for sequential functionalization, offering high stability under standard bench conditions and compatibility with diverse nucleophiles. This compound facilitates the synthesis of biologically relevant analogs in medicinal chemistry workflows.

Synthesis

  • Route1
    • 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Tofacitinib Impurity|CS-0213936
      3680-69-1
    • ~96%
    • In-stock
      4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine|CS-W005653
      115093-90-8

    References

    • Song, Yang; Ding, Haixin; Dou, Yanhui; Yang, Ruchun; Sun, Qi; Xiao, Qiang; Ju, Yong Synthesis, 2011 , # 9 art. no. F14911SS, p. 1442 - 1446
  • Route2

    References

    • Rawlins, David Brent; Voronkov, Michael Victor; Zhang, Yulian Patent: US2006/189638 A1, 2006 ; Location in patent: Page/Page column 10 ;
  • Route3
    • In-stock
      N-Chlorosuccinimide|CS-W020129
      128-09-6
    • 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Tofacitinib Impurity|CS-0213936
      3680-69-1
    • ~90%
    • In-stock
      4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine|CS-W005653
      115093-90-8

    References

    • Harrison, Bryce A.; Whitlock, N. Andrew; Voronkov, Michael V.; Almstead, Zheng Y.; Gu, Kun-Jian; Mabon, Ross; Gardyan, Michael; Hamman, Brian D.; Allen, Jason; Gopinathan, Suma; McKnight, Beth; Crist, Mike; Zhang, Yulian; Liu, Ying; Courtney, Lawrence F.; Key, Billie; Zhou, Julia; Patel, Nita; Yates, Phil W.; Liu, Qingyun; Wilson, Alan G. E.; Kimball, S. David; Crosson, Craig E.; Rice, Dennis S.; Rawlins, David B. Journal of Medicinal Chemistry, 2009 , vol. 52, # 21 p. 6515 - 6518

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   41.57
  • LogP   2.2647
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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