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CS-W001157 4
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Tert-butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

  • CAS No. 369638-69-7

  • Cat. No. CS-0451723
  • Molecule weight288.14
  • Purity≥97%
  • MDL No.None

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

Tert-butyl (5-(bromomethyl)pyrazin-2-yl)carbamate|CS-0451723

Structure of 369638-69-7

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General Information

  • CAS No. 369638-69-7
  • Cat. No. CS-0451723
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₄BrN₃O₂
  • Molecular Weight 288.14
  • Synonym(s) 2-Methyl-2-propanyl [5-(bromomethyl)-2-pyrazinyl]carbamate
  • SMILES CC(C)(OC(NC1=CN=C(C=N1)CBr)=O)C

Description

Tert-butyl (5-(bromomethyl)pyrazin-2-yl)carbamate features a bromomethyl group at the 5-position of a pyrazine ring, enabling direct functionalization in late-stage diversification. The tert-butyl carbamate handle offers stability and convenient deprotection under mild acidic conditions. This reagent integrates readily into synthetic sequences requiring selective alkylation or transition-metal-catalyzed coupling reactions.

Application

Tert-butyl (5-(bromomethyl)pyrazin-2-yl)carbamate serves as a versatile building block for the synthesis of pyrazine-based pharmaceutical intermediates and functionalized heterocycles. The bromomethyl group enables facile Suzuki, Stille, or nucleophilic substitution reactions, while the tert-butyl carbamate protects the pyrazin-2-amine nitrogen under standard conditions. Its bench-stable nature and compatibility with diverse coupling protocols make it ideal for iterative C–H functionalization and late-stage diversification in medicinal chemistry workflows.

Synthesis

  • Route1

    References

    • Lee, Jeewoo; Kang, Sang-Uk; Kil, Min-Jung; Shin, Myoungyoup; Lim, Ju-Ok; Choi, Hyun-Kyung; Jin, Mi-Kyoung; Kim, Su Yeon; Kim, Sung-Eun; Lee, Yong-Sil; Min, Kyung-Hoon; Kim, Young-Ho; Ha, Hee-Jin; Tran, Richard; Welter, Jacqueline D.; Wang, Yun; Szabo, Tamas; Pearce, Larry V.; Lundberg, Daniel J.; Toth, Attila; Pavlyukovets, Vladimir A.; Morgan, Matthew A.; Blumberg, Peter M. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 18 p. 4136 - 4142
  • Route2

    References

    • Shimamura, Tadashi; Shibata, Jun; Kurihara, Hideki; Mita, Takashi; Otsuki, Sachie; Sagara, Takeshi; Hirai, Hiroshi; Iwasawa, Yoshikazu Bioorganic and Medicinal Chemistry Letters, 2006 , vol. 16, # 14 p. 3751 - 3754

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: 3259
Class : 8
Packing Group : Ⅲ
Hazard Statements : H302-H314
Precautionary Statements : P260-P264-P270-P280-P301+P330+P331-P304+P340-P330-P363-P405-P501

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Computational Chemistry Data

  • TPSA   64.11
  • LogP   2.7185
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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