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CS-W001157 4
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4-Chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine

  • CAS No. 83942-13-6

  • Cat. No. CS-0054605
  • Purity≥98%
  • MDL No.None

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

4-Chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine|CS-0054605

Structure of 83942-13-6

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General Information

  • CAS No. 83942-13-6
  • Cat. No. CS-0054605
  • Purity ≥98%
  • MDL No. None
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₇ClN₂
  • Molecular Weight 154.60
  • Synonym(s) 4-Chloro-6,7-dihydro-5H-cyclopentapyrimidine
  • SMILES ClC1=NC=NC2=C1CCC2

Description

4-Chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine features a fused bicyclic core with a chlorine substituent at the 4-position, enabling direct incorporation into heterocyclic scaffolds. This bench-stable, moisture-tolerant building block facilitates efficient access to functionalized pyrimidine derivatives through palladium-catalyzed cross-coupling or nucleophilic substitution reactions.

Application

4-Chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine serves as a versatile building block for the synthesis of biologically active heterocycles, particularly in medicinal chemistry. Its reactive chlorine substituent enables facile nucleophilic substitution, facilitating the construction of diverse pyrimidine-based scaffolds. The saturated cyclopentane ring enhances metabolic stability and modulates physicochemical properties, supporting its use in lead optimization. Bench-stable and compatible with standard purification methods, it functions reliably in multi-step syntheses.

Synthesis

  • Route1

    References

    • ARRAY BIOPHARMA INC.; GENENTECH, INC.; MITCHELL, Ian, S.; BLAKE, James, F.; XU, Rui; KALLAN, Nicholas, C.; XIAO, Dengming; SPENCER, Keith, Lee; BENCSIK, Josef, R.; LIANG, Jun; SAFINA, Brian; ZHANG, Birong; CHABOT, Christine; DO, Steven Patent: WO2008/6040 A1, 2008 ; Location in patent: Page/Page column 40; 95 ; WO 2008/006040 A1
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 17 p. 6829 - 6844
  • Route3
    • Methyl 2-amino-1-cyclopentene-1-carboxylate|CS-0208640
      52909-60-1
    • ~%
    • In-stock
      4-Chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine|CS-0054605
      83942-13-6

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 17 p. 6829 - 6844

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   25.78
  • LogP   1.6187
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   0

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