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CS-W001157 4
Total: USD 88.00

Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate

  • CAS No. 776-53-4

  • Cat. No. CS-W008025
  • Purity≥98%
  • MDL No.MFCD00090781

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

Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate|CS-W008025

Structure of 776-53-4

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General Information

  • CAS No. 776-53-4
  • Cat. No. CS-W008025
  • Purity ≥98%
  • MDL No. MFCD00090781
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₁N₃O₂S
  • Molecular Weight 213.26
  • Synonym(s) Ethyl 4-amino-2-(methylthio)pyrimidine-5-carboxylate
  • SMILES O=C(C1=CN=C(SC)N=C1N)OCC

Description

Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate features a pyrimidine core functionalized with an amino group at C4, a methylthio substituent at C2, and an ethyl ester at C5. This combination enables direct incorporation into heterocyclic scaffolds via coupling reactions. The molecule exhibits enhanced solubility in common organic solvents and stability under standard bench conditions, facilitating use in synthetic medicinal chemistry workflows.

Application

Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient access to pyrimidine-based scaffolds. Its amino and methylthio groups offer orthogonal reactivity for selective functionalization, while the ester moiety facilitates downstream transformations. Bench-stable and readily purified, it functions effectively in coupling reactions, nucleophilic substitutions, and transition-metal-catalyzed processes common in medicinal chemistry and API development workflows.

Synthesis

  • Route1
    • Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate Avanafil  Impurity|CS-0228709
      5909-24-0
    • ~90%
    • In-stock
      Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate|CS-W008025
      776-53-4

    References

    • ELI LILLY AND COMPANY; DECIPHERA PHARMACEUTICALS, LLC; ALLGEIER, Matthew Carl; FLYNN, Daniel L.; KAUFMAN, Michael D.; PATEL, Phenil J.; WOLFANGEL, Craig D. Patent: WO2013/134243 A1, 2013 ; Location in patent: Page/Page column 15-16 ;
  • Route2
    • In-stock
      Ethyl 6-amino-2-thioxo-1,2-dihydropyrimidine-5-carboxylate|CS-0078660
      774-07-2
    • null|null
      74-88-4
    • ~96%
    • In-stock
      Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate|CS-W008025
      776-53-4

    References

    • Lang, Hengyuan; Lan, Jiong; Fang, Yunfeng Patent: US2005/20590 A1, 2005 ; Location in patent: Page/Page column 27 ; US 20050020590 A1
  • Route3
    • null|null
      1336-21-6
    • Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate Avanafil  Impurity|CS-0228709
      5909-24-0
    • ~78%
    • In-stock
      Ethyl 4-amino-2-(methylthio)pyrimidin-5-carboxylate|CS-W008025
      776-53-4

    References

    • Warner-Lambert Company Patent: US6498163 B1, 2002 ; US 6498163 B1

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   78.1
  • LogP   0.9574
  • H_Acceptors   6
  • H_Donors   1
  • Rotatable_Bonds   3

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