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Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate

  • CAS No. 1224944-77-7

  • Cat. No. CS-D0465
  • Purity≥98%
  • MDL No.MFCD12407819

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

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate|CS-D0465

Structure of 1224944-77-7

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General Information

  • CAS No. 1224944-77-7
  • Cat. No. CS-D0465
  • Purity ≥98%
  • MDL No. MFCD12407819
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₈ClN₃O₂
  • Molecular Weight 225.63
  • Synonym(s) thyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate
  • SMILES O=C(C1=C2N=C(Cl)C=CN2N=C1)OCC

Description

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate features a chlorinated pyrazolopyrimidine core that enables direct functionalization at the 5-position. This electron-deficient heterocycle integrates readily into synthetic sequences requiring stable, bench-stable building blocks for medicinal chemistry and materials development.

Application

Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate serves as a versatile building block for constructing biologically relevant heterocyclic scaffolds. The chloro group at the 5-position enables nucleophilic substitution reactions, facilitating the introduction of diverse substituents under mild conditions. Its ester functionality supports subsequent transformations such as hydrolysis or reduction, while the pyrazolopyrimidine core exhibits excellent bench stability and compatibility with standard synthetic protocols. This compound functions effectively in medicinal chemistry campaigns targeting kinase inhibitors and other pharmaceutical candidates.

Synthesis

  • Route1

    References

    • ARRAY BIOPHARMA INC.; ALLEN, Shelley; ANDREWS, Steven S.; CONDROSKI, Kevin Ronald; HAAS, Julia; HUANG, Lily; JIANG, Yutong; KERCHER, Timothy; SEO, Jeongbeob Patent: WO2011/6074 A1, 2011 ; Location in patent: Page/Page column 70-71 ;
  • Route2
    • Ethyl 3-amino-1H-pyrazole-4-carboxylate Allopurinol Impurity|CS-0229741
      6994-25-8
    • ~%
    • In-stock
      Ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate|CS-D0465
      1224944-77-7

    References

    • WO2011/6074 A1, ;
  • Route3

    References

    • WO2013/59587 A1, ;

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   56.49
  • LogP   1.5594
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   2

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