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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine

  • CAS No. 1169690-88-3

  • Cat. No. CS-0051655
  • Purity≥97%
  • MDL No.None

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine|CS-0051655

Structure of 1169690-88-3

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General Information

  • CAS No. 1169690-88-3
  • Cat. No. CS-0051655
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆BN₃O₂
  • Molecular Weight 245.09
  • Synonym(s) Pyrazolo1,5-apyrimidine-3-boronic acid picol ester
  • SMILES CC1(C)OB(OC1(C)C)C1=C2N=CC=CN2N=C1

Description

This pyrazolo[1,5-a]pyrimidine derivative features a tetramethylborolane handle enabling efficient Suzuki-Miyaura coupling under standard conditions. The electron-deficient heterocyclic core supports modular functionalization and integrates readily into bioactive scaffolds.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. Its stability under ambient conditions and tolerance to diverse functional groups enable efficient construction of biaryl scaffolds in medicinal chemistry and materials science. The tetramethyl-substituted dioxaborolane moiety enhances reactivity while minimizing protodeboronation, making it ideal for sequential coupling strategies and late-stage functionalization.

Synthesis

  • Route1

    References

    • VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2009/85913 A1, 2009 ; Location in patent: Page/Page column 68; 69-70 ; WO 2009/085913 A1

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   48.65
  • LogP   1.0285
  • H_Acceptors   5
  • H_Donors   0
  • Rotatable_Bonds   1

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