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Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate

  • CAS No. 53135-24-3

  • Cat. No. CS-0046031
  • Purity≥97%
  • MDL No.None

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

Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate|CS-0046031

Structure of 53135-24-3

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General Information

  • CAS No. 53135-24-3
  • Cat. No. CS-0046031
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₀N₂O₃
  • Molecular Weight 182.18
  • Synonym(s) 5-PyriMidinecarboxylic acid, 3,4-dihydro-2-Methyl-4-oxo-, ethyl ester
  • SMILES O=C(C1=CN=C(C)NC1=O)OCC.[Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate]

Description

Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate features a versatile dihydropyrimidine core with a ketone at C6 and an ester at C5, enabling direct integration into heterocyclic synthesis. The methyl group at C2 enhances regioselectivity in cycloadditions and condensations. This bench-stable, moisture-tolerant building block facilitates efficient access to functionalized pyrimidines under standard conditions.

Application

Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine-based scaffolds via condensation and cyclization reactions. Its enolizable C6 carbonyl and electron-deficient C5 position facilitate nucleophilic addition and Michael-type reactions, while the ester group supports subsequent functionalization. Bench-stable and readily purified by recrystallization or chromatography, it functions effectively in multistep syntheses of bioactive molecules and pharmaceutical intermediates.

Synthesis

  • Route1
    • null|null
      124-42-5
    • In-stock
      Diethyl 2-(ethoxymethylene)malonate|CS-0019402
      87-13-8
    • ~27%
    • In-stock
      Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate|CS-0046031
      53135-24-3

    References

    • Corvas International, Inc. Patent: US5656645 A1, 1997 ; US 5656645 A
  • Route2

    References

    • Corvas International, Inc. Patent: US6011158 A1, 2000 ;
  • Route3
    • null|null
      143-37-3
    • In-stock
      Diethyl 2-(ethoxymethylene)malonate|CS-0019402
      87-13-8
    • ~%
    • In-stock
      Ethyl 2-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylate|CS-0046031
      53135-24-3

    References

    • Bioorganic and Medicinal Chemistry Letters, , vol. 12, # 3 p. 403 - 406

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   0.25502
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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