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CS-W001157 4
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N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine

  • CAS No. 186692-41-1

  • Cat. No. CS-M0067
  • Purity≥98%
  • MDL No.MFCD00674111

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

N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine|CS-M0067

Structure of 186692-41-1

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General Information

  • CAS No. 186692-41-1
  • Cat. No. CS-M0067
  • Purity ≥98%
  • MDL No. MFCD00674111
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₆ClN₅
  • Molecular Weight 301.77
  • Synonym(s) 6-benzylamino-2-chloro-9-isopropylpurine
  • SMILES ClC1=NC(NCC2=CC=CC=C2)=C3C(N(C(C)C)C=N3)=N1

Description

N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine features a purine core functionalized with a chloro group at C2 and an isopropyl substituent at C9, enhancing solubility and metabolic stability. The N-benzyl moiety imparts favorable π-stacking interactions and improved lipophilicity for target engagement in kinase inhibition studies. This compound serves as a key scaffold in the development of ATP-competitive inhibitors.

Application

N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine serves as a versatile purine scaffold for medicinal chemistry applications, enabling direct functionalization at the 6-position via nucleophilic substitution. The 2-chloro group exhibits high reactivity under mild conditions, facilitating efficient coupling with diverse amines and heterocycles. Bench-stable and easily purified by flash chromatography, it functions as a key building block in the synthesis of kinase inhibitors and other purine-based bioactive molecules.

Synthesis

  • Route1
    • N-Benzyl-2-chloro-9H-purin-6-amine|CS-M0066
      39639-47-9
    • null|null
      75-26-3
    • ~86%
    • In-stock
      N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine|CS-M0067
      186692-41-1

    References

    • Oumata, Nassima; Ferandin, Yoan; Meijer, Laurent; Galons, Herve Organic Process Research and Development, 2009 , vol. 13, # 3 p. 641 - 644
  • Route2
    • null|null
      100-46-9
    • In-stock
      2,6-Dichloro-9-isopropyl-9H-purine|CS-D1268
      203436-45-7
    • ~%
    • In-stock
      N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine|CS-M0067
      186692-41-1

    References

    • Travnicek, Zdenek; Popa, Igor; Cajan, Michal; Zboril, Radek; Krystof, Vladimir; Mikulik, Jiri Journal of Inorganic Biochemistry, 2010 , vol. 104, # 4 p. 405 - 417
  • Route3
    • N-Benzyl-2-chloro-9H-purin-6-amine|CS-M0066
      39639-47-9
    • ~%
    • In-stock
      N-Benzyl-2-chloro-9-isopropyl-9H-purin-6-amine|CS-M0067
      186692-41-1

    References

    • Oh, Chang-Hyun; Lee, Su-Chul; Lee, Ki-Soo; Woo, Eun-Rhan; Hong, Chang Yong; Yang, Boem-Seok; Baek, Dae Jin; Cho, Jung-Hyuck Archiv der Pharmazie, 1999 , vol. 332, # 6 p. 187 - 190

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-P361-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   55.63
  • LogP   3.6727
  • H_Acceptors   5
  • H_Donors   1
  • Rotatable_Bonds   4

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