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4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine

  • CAS No. 582313-57-3

  • Cat. No. CS-0054793
  • Purity≥96%
  • MDL No.None

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

4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine|CS-0054793

Structure of 582313-57-3

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General Information

  • CAS No. 582313-57-3
  • Cat. No. CS-0054793
  • Purity ≥96%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃ClFN₃
  • Molecular Weight 171.56
  • Synonym(s) 7H-Pyrrolo[2,3-d]pyrimidine,4-chloro-5-fluoro-
  • SMILES FC1=CNC2=C1C(Cl)=NC=N2

Description

4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine is a heterocyclic building block featuring orthogonal halogen handles for selective functionalization. This electron-deficient scaffold enables efficient coupling in cross-coupling reactions and serves as a key intermediate in the synthesis of kinase inhibitors and nucleoside analogs.

Application

4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine serves as a versatile building block in medicinal chemistry, enabling efficient construction of purine-based scaffolds. Its orthogonal halogenation pattern facilitates palladium-catalyzed cross-coupling reactions and nucleophilic substitution, offering high functional group tolerance and bench stability. This compound functions as a key intermediate in the synthesis of kinase inhibitors and antiviral agents, with predictable reactivity under standard conditions.

Synthesis

  • Route1
    • 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Tofacitinib Impurity|CS-0213936
      3680-69-1
    • ~59%
    • In-stock
      4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine|CS-0054793
      582313-57-3

    References

    • Hu, Weidong; Wang, Ping'An; Song, Chuanjun; Pan, Zhenliang; Wang, Qiang; Guo, Xiaohe; Yu, Xuejun; Shen, Zhenhua; Wang, Shuyang; Chang, Junbiao Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 24 p. 7297 - 7298
  • Route2

    References

    • MICROLOGIX BIOTECH INC. Patent: WO2004/11478 A2, 2004 ; Location in patent: Page 27 ;
  • Route3
    • null|null
      582313-56-2
    • ~%
    • In-stock
      4-Chloro-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine|CS-0054793
      582313-57-3

    References

    • WO2006/65335 A2, ; Page/Page column 21; 22 ; WO 2006/065335 A2

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

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Computational Chemistry Data

  • TPSA   41.57
  • LogP   1.7504
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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