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CS-W001157 4
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Ethyl4-hydroxy-2-oxo-1,2-dihydropyrimidine-5-carboxylate

  • CAS No. 28485-17-8

  • Cat. No. CS-0042918
  • Molecule weight184.15
  • Purity≥95%
  • MDL No.MFCD00057337

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

Ethyl4-hydroxy-2-oxo-1,2-dihydropyrimidine-5-carboxylate|CS-0042918

Structure of 28485-17-8

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General Information

  • CAS No. 28485-17-8
  • Cat. No. CS-0042918
  • Purity ≥95%
  • MDL No. MFCD00057337
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₈N₂O₄
  • Molecular Weight 184.15
  • Synonym(s) Ethyluracil-5-carboxylate
  • SMILES O=C(C1=CNC(N=C1O)=O)OCC

Description

Ethyl 4-hydroxy-2-oxo-1,2-dihydropyrimidine-5-carboxylate serves as a key heterocyclic scaffold in medicinal chemistry, featuring a hydroxyl group at C4 and a carbonyl at C2 that enable diverse functionalization. This bench-stable intermediate integrates readily into synthetic sequences for pyrimidine-based bioactive compounds.

Application

Ethyl 4-hydroxy-2-oxo-1,2-dihydropyrimidine-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine-based scaffolds. The molecule features orthogonal functional groups—carboxylate ester and enolizable C4 hydroxyl—that facilitate sequential transformations. It participates reliably in nucleophilic additions, condensations, and cyclizations under mild conditions, with demonstrated stability for bench storage and straightforward purification. Widely used in medicinal chemistry and agrochemical research, it functions as a key intermediate in the construction of bioactive pyrimidines.

Synthesis

  • Route1

    References

    • VERTEX PHARMACEUTICALS INCORPORATED; WANG, Tiansheng; HANZELKA, Brian; MUH, Ute; BEMIS, Guy; ZUCCOLA, Harmon, J. Patent: WO2011/19405 A1, 2011 ; Location in patent: Page/Page column 119 ; WO 2011/019405 A1
  • Route2
    • Ethyl 4-isopropyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate|CS-0617084
      198826-86-7
    • ~74%
    • In-stock
      Ethyl4-hydroxy-2-oxo-1,2-dihydropyrimidine-5-carboxylate|CS-0042918
      28485-17-8

    References

    • Shanmugam, Pachaiyappan; Perumal, Paramasivan T. Tetrahedron, 2007 , vol. 63, # 3 p. 666 - 672
  • Route3
    • null|null
      17994-57-9
    • ~71%
    • In-stock
      Ethyl4-hydroxy-2-oxo-1,2-dihydropyrimidine-5-carboxylate|CS-0042918
      28485-17-8

    References

    • Shanmugam, Pachaiyappan; Perumal, Paramasivan T. Tetrahedron, 2007 , vol. 63, # 3 p. 666 - 672

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   92.28
  • LogP   -0.3478
  • H_Acceptors   5
  • H_Donors   2
  • Rotatable_Bonds   2

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