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Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate

  • CAS No. 95928-49-7

  • Cat. No. CS-0045763
  • Purity≥97%
  • MDL No.MFCD09863163

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

Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate|CS-0045763

Structure of 95928-49-7

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General Information

  • CAS No. 95928-49-7
  • Cat. No. CS-0045763
  • Purity ≥97%
  • MDL No. MFCD09863163
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈N₂O₃
  • Molecular Weight 168.15
  • Synonym(s) Ethyl 2-hydroxypyrimidine-5-carboxylate
  • SMILES O=C(C1=CNC(N=C1)=O)OCC

Description

Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate serves as a key scaffold in heterocyclic synthesis, featuring a conjugated enone system and a pendant ester group. This bench-stable compound integrates readily into multistep transformations, enabling efficient access to pyrimidine-based architectures through nucleophilic addition and cyclization pathways.

Application

Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine scaffolds prevalent in medicinal chemistry. Its enolizable carbonyl and electron-deficient C5 position facilitate nucleophilic addition and condensation reactions. The molecule exhibits bench stability, ease of purification, and compatibility with standard reaction conditions, making it ideal for constructing biologically relevant frameworks through modular synthetic approaches.

Synthesis

  • Route1

    References

    • Qian, Changgeng; Cai, Xiong; Zhai, Haixiao Patent: US2009/76006 A1, 2009 ; Location in patent: Page/Page column 31; 40 ; US 20090076006 A1
  • Route2

    References

    • Chemical and Pharmaceutical Bulletin, , vol. 48, # 10 p. 1504 - 1513
  • Route3
    • Ethyl (Z)-2-(ethoxymethyl)-3-methoxyacrylate|CS-0138785
      879008-23-8
    • ~%
    • In-stock
      Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate|CS-0045763
      95928-49-7

    References

    • WO2011/130628 A1, ; WO 2011/130628 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   72.05
  • LogP   -0.0534
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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