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Paper | Regular issue | Vol 60, No. 11, 2003, pp.2511-2517
Published online, 5th September, 2003
DOI: 10.3987/COM-03-9872
Synthesis of the Tetrahydropteridine-2,4-dione Having a Substituted Methyl Group at 6-Position

Masaru Tada,* Tomoyuki Shimamura, and Takeaki Suzuki

*Department of Chemistry, School of Science and Engineering, Waseda University, Shinjuku-ku, Tokyo 169-8555, Japan

Abstract

Lewis acid treatment of 5-amino-6-(N-2,3-epoxypropyl-N-tosyl)amino-1,3-dimethyluracil (3) gave the diazepine (4) fused to uracil ring, and the tosylate (5) from 4 underwent ring transformation to provide tetrahydropteridinediones (7 and 8) depending on the reaction conditions. Thus, heating in dry acetonitrile led to 6-tosyloxymethyltetrahydropteridine-2,4-dione (7) whereas that in wet acetonitrile to 6-hydroxymethyl derivative (8).