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Paper | Regular issue | Vol 48, No. 6, 1998, pp.1157-1167
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8117
Synthesis of Thieno[2,3-d]pyrimidines and Aminopyrimidines from 2-Alkoxy-5-cyano-4-thioxopyrimidine Intermediates

Matthias Rehwald* and Karl Gewald

*Department of Organic Chemistry, Technical University of Dresden, Mommsenstrasse 13, D-01062 Dresden, Germany

Abstract

β-Chloro-α-cyanocinnamonitrile reacts in an one-pot reaction with potassium thiocyanate and alkanol to form 2-alkoxy-6-phenyl-5-cyano-1,4-dihydro-4-pyrimidinthiones. The products were S-alkylated to yield thieno[2,3-d]pyrimidines on cyclization and aminopyrimidines on substitution of alkoxy and alkylthio groups.