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4,6-Dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine

  • CAS No. 21254-22-8

  • Cat. No. CS-0154198
  • Purity≥98%
  • MDL No.MFCD12405952

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

4,6-Dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine|CS-0154198

Structure of 21254-22-8

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General Information

  • CAS No. 21254-22-8
  • Cat. No. CS-0154198
  • Purity ≥98%
  • MDL No. MFCD12405952
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₈Cl₂N₄
  • Molecular Weight 231.08
  • Synonym(s) 4,6-dichloro-1-propan-2-ylpyrazolo[3,4-d]pyrimidine
  • SMILES CC(C)N1C2=NC(=NC(=C2C=N1)Cl)Cl

Description

4,6-Dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine features a sterically hindered isopropyl group and electron-deficient pyrazolopyrimidine core, enabling selective coupling in kinase inhibitor scaffolds. This bench-stable heterocycle integrates readily into medicinal chemistry campaigns requiring halogen-directed functionalization under standard conditions.

Application

4,6-Dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine serves as a versatile building block in medicinal chemistry, enabling efficient construction of purine-like scaffolds via nucleophilic substitution. The dichloro functionality provides orthogonal reactivity for sequential functionalization, while the isopropyl group enhances solubility and stability. This compound facilitates rapid diversification in kinase inhibitor and antiviral agent development, offering reliable performance in standard coupling protocols and robust bench handling.

Synthesis

  • Route1
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      2257-52-5
    • In-stock
      2,4,6-Trichloropyrimidine-5-carbaldehyde|CS-M0311
      50270-27-4
    • ~%
    • In-stock
      4,6-Dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine|CS-0154198
      21254-22-8

    References

    • Curran, Kevin J.; Verheijen, Jeroen C.; Kaplan, Joshua; Richard, David J.; Toral-Barza, Lourdes; Hollander, Irwin; Lucas, Judy; Ayral-Kaloustian, Semiramis; Yu, Ker; Zask, Arie Bioorganic and Medicinal Chemistry Letters, 2010 , vol. 20, # 4 p. 1440 - 1444
  • Route2
    • null|null
      21254-21-7
    • ~%
    • In-stock
      4,6-Dichloro-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidine|CS-0154198
      21254-22-8

    References

    • Schmidt et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1052,1056 Helvetica Chimica Acta, 1959 , vol. 42, p. 349,354
  • Route3

    References

    • Schmidt et al. Helvetica Chimica Acta, 1958 , vol. 41, p. 1052,1056 Helvetica Chimica Acta, 1959 , vol. 42, p. 349,354

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H311-H331
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P361+P364-P405-P501

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Computational Chemistry Data

  • TPSA   43.6
  • LogP   2.714
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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