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4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine

  • CAS No. 35808-68-5

  • Cat. No. CS-W009106
  • Purity≥95%
  • MDL No.MFCD09033903

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

4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine|CS-W009106

Structure of 35808-68-5

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General Information

  • CAS No. 35808-68-5
  • Cat. No. CS-W009106
  • Purity ≥95%
  • MDL No. MFCD09033903
  • Storage -20°C, sealed storage, away from moisture
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆ClN₃
  • Molecular Weight 167.60
  • Synonym(s) 4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine; NSC 344519; 4-chloro-6-methyl-1H-pyrrolo[2,3-d]pyrimidine
  • SMILES CC1=CC2=C(Cl)N=CN=C2N1

Description

4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine serves as a pivotal heterocyclic scaffold in medicinal chemistry, offering a rigid, electron-deficient core for targeted molecular design. This compound integrates readily into kinase inhibitors and antiviral agents, leveraging its ability to form key hydrogen bonds and π-stacking interactions within biological binding sites.

Application

4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine serves as a versatile heterocyclic building block in medicinal chemistry, enabling efficient access to purine-like scaffolds. Its chlorine atom facilitates nucleophilic substitution under mild conditions, while the methyl group enhances metabolic stability and modulates electronic properties. The scaffold exhibits excellent bench stability and compatibility with standard coupling reactions, making it well-suited for the synthesis of kinase inhibitors and other bioactive molecules.

Synthesis

  • Route1
    • 4-Chloro-6-methyl-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine|CS-0320596
      252723-16-3
    • ~89%
    • In-stock
      4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine|CS-W009106
      35808-68-5

    References

    • Sunesis Pharmaceuticals, Inc Patent: US2009/5359 A1, 2009 ; Location in patent: Page/Page column 26 ; US 20090005359 A1
  • Route2
    • 6-Methyl-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one|CS-0067234
      99898-85-8
    • ~48%
    • In-stock
      4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine|CS-W009106
      35808-68-5

    References

    • Harrison, Bryce A.; Whitlock, N. Andrew; Voronkov, Michael V.; Almstead, Zheng Y.; Gu, Kun-Jian; Mabon, Ross; Gardyan, Michael; Hamman, Brian D.; Allen, Jason; Gopinathan, Suma; McKnight, Beth; Crist, Mike; Zhang, Yulian; Liu, Ying; Courtney, Lawrence F.; Key, Billie; Zhou, Julia; Patel, Nita; Yates, Phil W.; Liu, Qingyun; Wilson, Alan G. E.; Kimball, S. David; Crosson, Craig E.; Rice, Dennis S.; Rawlins, David B. Journal of Medicinal Chemistry, 2009 , vol. 52, # 21 p. 6515 - 6518
  • Route3
    • 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine Tofacitinib Impurity|CS-0213936
      3680-69-1
    • ~%
    • In-stock
      4-Chloro-6-methyl-7H-pyrrolo[2,3-d]pyrimidine|CS-W009106
      35808-68-5

    References

    • WO2012/158795 A1, ; WO 2012/158795 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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   41.57
  • LogP   1.91972
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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