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CS-W001157 4
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Ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

  • CAS No. 33458-27-4

  • Cat. No. CS-0138792
  • Purity≥96%
  • MDL No.MFCD10688281

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

Ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate|CS-0138792

Structure of 33458-27-4

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General Information

  • CAS No. 33458-27-4
  • Cat. No. CS-0138792
  • Purity ≥96%
  • MDL No. MFCD10688281
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₁₀N₂O₃
  • Molecular Weight 170.17
  • Synonym(s) None
  • SMILES O=C1NCC(C(OCC)=O)=CN1

Description

Ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate serves as a key heterocyclic scaffold in medicinal chemistry, integrating a carbonyl group at C2 and an ester functionality at C5. This bench-stable compound enables efficient access to pyrimidine-based pharmacophores through modular transformations.

Application

Ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine-based scaffolds. Its dual functionality—enolizable carbonyl and ester group—facilitates nucleophilic addition, alkylation, and cyclization reactions under mild conditions. The compound exhibits good bench stability and is compatible with standard purification methods, making it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

  • Route1
    • Ethyl (Z)-2-(ethoxymethyl)-3-methoxyacrylate|CS-0138785
      879008-23-8
    • In-stock
      Urea|CS-B1800
      57-13-6
    • ~65%
    • In-stock
      Ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate|CS-0138792
      33458-27-4

    References

    • CURIS, INC. Patent: WO2009/36016 A1, 2009 ; Location in patent: Page/Page column 69 ;
  • Route2
    • null|null
      2974-30-3
    • In-stock
      Urea|CS-B1800
      57-13-6
    • ~64%
    • In-stock
      Ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate|CS-0138792
      33458-27-4

    References

    • Ohta, Kiminori; Kawachi, Emiko; Inoue, Noriko; Fukasawa, Hiroshi; Hashimoto, Yuichi; Itai, Akiko; Kagechika, Hiroyuki Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 10 p. 1504 - 1513
  • Route3

    References

    • Leclerc, Jean-Philippe; Li, Chun Sing; Ramtohul, Yeeman K. Patent: US2011/152295 A1, 2011 ;

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
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   67.43
  • LogP   -0.2538
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   2

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