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CS-W001157 4
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Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate

  • CAS No. 6153-44-2

  • Cat. No. CS-0008570
  • Purity≥95%
  • MDL No.MFCD00127824

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

Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate|CS-0008570

Structure of 6153-44-2

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General Information

  • CAS No. 6153-44-2
  • Cat. No. CS-0008570
  • Purity ≥95%
  • MDL No. MFCD00127824
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₆N₂O₄
  • Molecular Weight 170.12
  • Synonym(s) Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate; Methyl orotate; 4-Pyrimidinecarboxylic acid, 1,2,3,6-tetrahydro-2,6-dioxo-, methyl ester
  • SMILES O=C(C(NC1=O)=CC(N1)=O)OC

Description

Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate features a uniquely reactive pyrimidine core with adjacent carbonyl and ester functionalities. This bench-stable heterocycle integrates readily into multicomponent condensations, serving as a versatile synthon for nitrogen-rich scaffolds in medicinal chemistry and materials synthesis.

Application

Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine cores via standard condensation and cyclization protocols. Its dual carbonyl and ester functionalities offer orthogonal reactivity for functional group manipulation, while its bench stability and straightforward purification support reliable use in medicinal chemistry and process development workflows.

Synthesis

  • Route1
    • null|null
      67-56-1
    • In-stock
      Orotic acid|CS-2314
      65-86-1
    • ~92%
    • In-stock
      Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate|CS-0008570
      6153-44-2

    References

    • Hudson, Robert H. E.; Wojciechowski, Filip Canadian Journal of Chemistry, 2005 , vol. 83, # 10 p. 1731 - 1740
  • Route2
    • null|null
      80140-18-7
    • ~84%
    • In-stock
      Methyl 2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylate|CS-0008570
      6153-44-2

    References

    • DeFrees, Shawn A.; Reddy, Kalakota S.; Cassady, John M. Synthetic Communications, 1988 , vol. 18, # 2 p. 213 - 220
  • Route3

    References

    • Heterocycles, , vol. 67, # 1 p. 135 - 160

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

Quality Control

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Computational Chemistry Data

  • TPSA   92.02
  • LogP   -1.1502
  • H_Acceptors   4
  • H_Donors   2
  • Rotatable_Bonds   1

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