Synthesis of 2-alkylthio-6-amino-9-(2-hydroxylethyl)purines
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R973.2

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    Abstract:

    2-Amino-6-chloropurine as the starting material was treated with 2-bromoethyl acetate to product 9-acetoxyethyl-2-amino-6-chloropurine (Ⅰ, 65.6% yield). Compound Ⅰwas diazotized and reacted with disulfides to afford 9-acetoxyethyl-2-alkythio-6-chloropurine (Ⅱ, 58.3-72.1% yield). NaN3 was reacted with Ⅱto acquire 9-acetoxyethyl-2-alkythio-6-triazo purine (Ⅲ, 86.4-92.0% yield). The result of NMR test (Ⅲ)showed that there were azido tautomer(A)and tetrazolyl tautomer(T) in the solution, and the ratio of azido tautomer was 61.5-67.2%. We use PPh3-HCl-DMSO as the reaction solvent to reduced trizao to amino and hydrolyzed the ester completely to afford the 2-alkylthio-6-amino-9- (2-hydroxylethyl)purines (Ⅳ) in the good yield(~90%) in one pot. All the compounds synthesized were comfirmed through IR, 1H NMR, 13C NMR, and HRMS.

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History
  • Received:April 01,2014
  • Revised:April 29,2014
  • Adopted:May 19,2014
  • Online: August 05,2014
  • Published:
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