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2-(4-Methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

  • CAS No. 942922-07-8

  • Cat. No. CS-0091577
  • Purity≥97%
  • MDL No.MFCD08669592

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

2-(4-Methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine|CS-0091577

Structure of 942922-07-8

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General Information

  • CAS No. 942922-07-8
  • Cat. No. CS-0091577
  • Purity ≥97%
  • MDL No. MFCD08669592
  • Storage -20°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₂₅BN₄O₂
  • Molecular Weight 304.20
  • Synonym(s) 2-(4-METHYLPIPERAZIN-1-YL)PYRIMIDINE-5-BORONIC ACID PINACOL ESTER
  • SMILES CC1(C)C(C)(C)OB(C2=CN=C(N3CCN(C)CC3)N=C2)O1

Description

This pyrimidine derivative features a 4-methylpiperazine moiety paired with a boronate ester group, enabling efficient Suzuki-Miyaura cross-coupling under standard conditions. The tetramethyl-substituted dioxaborolane enhances stability and reactivity, while the electron-rich piperazine facilitates functionalization in late-stage diversification. Designed for streamlined synthesis in medicinal chemistry and materials science.

Application

2-(4-Methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pyrimidine core provides a rigid, electron-deficient scaffold compatible with diverse nucleophiles, while the pinacol boronate ester ensures excellent stability and ease of handling. This compound facilitates efficient C–C bond formation under mild conditions, enabling rapid access to functionalized heterocyclic architectures relevant in medicinal chemistry and materials science.

Synthesis

  • Route1
    • 5-Bromo-2-(4-methylpiperazin-1-yl)pyrimidine|CS-0148848
      141302-36-5
    • In-stock
      Bis(pinacolato)diborane|CS-D1216
      73183-34-3
    • ~%
    • In-stock
      2-(4-Methylpiperazin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine|CS-0091577
      942922-07-8

    References

    • WO2009/74812 A1, ; Page/Page column 68 ; WO 2009/074812 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

Quality Control

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Computational Chemistry Data

  • TPSA   50.72
  • LogP   0.5276
  • H_Acceptors   6
  • H_Donors   0
  • Rotatable_Bonds   2

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