Synthesis of N6-[endo-2'-(endo-5'-Hydroxy)norbornyl]-8-(N-methylisopropylamino)-9-methyladenine (WRC-0571): A potent and selective adenosine A1 receptor antagonist

Ken S. Rehder; Jason P. Burgess; Chunyang Jin; Chunyang Jin; Jason P. Burgess; Ken S. Rehder; George Brine

Synthesis of N6-[endo-2'-(endo-5'-Hydroxy)norbornyl]-8-(N-methylisopropylamino)-9-methyladenine (WRC-0571)

A potent and selective adenosine A1 receptor antagonist

Jin, C., Burgess, J., Rehder, K., & Brine, G. (2007). Synthesis of N6-[endo-2'-(endo-5'-Hydroxy)norbornyl]-8-(N-methylisopropylamino)-9-methyladenine (WRC-0571): A potent and selective adenosine A1 receptor antagonist. Synthesis, 2007(2), 219-224. https://doi.org/10.1055/s-2006-958939

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Abstract

A new versatile synthesis of N6-[endo-2'-(endo-5'-hydroxy)norbornyl]-8-(N-methylisopropylamino)-9-methyladenine (WRC-0571), a highly potent and selective antagonist for adenosine A1 receptor, is presented. The overall yield is 14%. The key step involved the stereoselective reduction of endo-2-(diphenylmethylamino)norbornan-5-one to generate the endo-5-hydroxy substituent using the Luche reagent (NaBH4-CeCl3) at -40 °C.