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tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

  • CAS No. 635698-56-5

  • Cat. No. CS-D0280
  • Purity≥97%
  • MDL No.MFCD08273933

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

tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate|CS-D0280

Structure of 635698-56-5

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General Information

  • CAS No. 635698-56-5
  • Cat. No. CS-D0280
  • Purity ≥97%
  • MDL No. MFCD08273933
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅Cl₂N₃O₂
  • Molecular Weight 304.17
  • Synonym(s) 2-Methyl-2-propanyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate
  • SMILES O=C(N1CCC2=NC(Cl)=NC(Cl)=C2C1)OC(C)(C)C

Description

tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate is a bench-stable, moisture-tolerant heterocyclic building block featuring two chlorine substituents at electron-deficient positions. This dihydro-pyrimidine scaffold integrates readily into medicinal chemistry campaigns, enabling efficient access to kinase-inhibitor scaffolds through straightforward deprotection and functionalization.

Application

tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate serves as a versatile building block for the synthesis of pyrido[4,3-d]pyrimidine scaffolds, enabling efficient functionalization at C2 and C4 positions. Its dichloro substitution pattern facilitates sequential cross-coupling reactions and nucleophilic displacement, while the tert-butyl ester group provides stability and ease of removal under mild acidic conditions. This compound demonstrates excellent bench stability and compatibility with diverse reaction conditions, making it well-suited for iterative synthesis in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • KYOWA HAKKO KOGYO CO., LTD. Patent: EP1552842 A1, 2005 ; Location in patent: Page/Page column 316 ;
  • Route2
    • 2,4-Dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine|CS-D0513
      726697-13-8
    • In-stock
      Di-tert-butyl dicarbonate|CS-0017817
      24424-99-5
    • ~73%
    • In-stock
      tert-Butyl 2,4-dichloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate|CS-D0280
      635698-56-5

    References

    • ZHOU, Han-Jie; PARLATI, Francesco; WUSTROW, David Patent: WO2014/15291 A1, 2014 ; Location in patent: Page/Page column 172; 173 ;
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 55, # 24 p. 10958 - 10971

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-H332-H335
Precautionary Statements : P261-P280-P338-P351

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Computational Chemistry Data

  • TPSA   55.32
  • LogP   3.0766
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   0

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