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5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine

  • CAS No. 87789-35-3

  • Cat. No. CS-0150091
  • Purity≥98%
  • MDL No.MFCD18642493

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

5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine|CS-0150091

Structure of 87789-35-3

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General Information

  • CAS No. 87789-35-3
  • Cat. No. CS-0150091
  • Purity ≥98%
  • MDL No. MFCD18642493
  • Storage -20°C, stored under nitrogen, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃Cl₂N₃S₂
  • Molecular Weight 252.14
  • Synonym(s) None
  • SMILES CSC1=NC2=NC(=NC(=C2S1)Cl)Cl

Description

5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine features a fused thiazolopyrimidine core with dual chloro substituents at electron-rich positions and a methylthio group at C2. This configuration imparts high reactivity in nucleophilic substitution and transition metal-catalyzed coupling reactions. The molecule exhibits excellent bench stability and solubility in common organic solvents, enabling seamless integration into synthetic sequences for pharmaceutical intermediates and functional materials.

Application

5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine serves as a versatile building block for heterocyclic synthesis, enabling efficient construction of advanced pyrimidine-based scaffolds. The dichloro substitution pattern facilitates nucleophilic displacement reactions, while the methylthio group offers orthogonal reactivity and bench stability. This compound functions as a key intermediate in the development of biologically active molecules, particularly in medicinal chemistry workflows requiring precise functionalization and compatibility with standard coupling protocols.

Synthesis

  • Route1

    References

    • GENENTECH, INC.; F. HOFFMANN - LA ROCHE AG Patent: WO2009/42607 A1, 2009 ; Location in patent: Page/Page column 94-95 ; WO 2009/042607 A1
  • Route2
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    • In-stock
      5,7-Dichloro-2-(methylthio)thiazolo[4,5-d]pyrimidine|CS-0150091
      87789-35-3

    References

    • Walek, Wolfgang Zeitschrift fuer Chemie (Stuttgart, Germany), 1983 , vol. 23, # 5 p. 179 - 180

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   38.67
  • LogP   3.115
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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