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Communication | Regular issue | Vol 36, No. 5, 1993, pp.923-927
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6230
Study of Thiazolo[4,5-d]pyrimidines: The Synthesis of Thiazolo[4,5-d]pyrimidine-2,7-diones and Novel Ring Opening to 2,4-Thiazolidinedione

Katsuhiko Nagahara,* Masae Sekine, Atsushi Takada, Howard B. Cottam, and Roland K. Robins

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Treatment of 7-oxo-3-phenylthiazolo[4,5-d]pyrimidine-2(6H)-thione (1) with dimethyl sulfate afforded 6-methyl-3-phenylthiazolo[4,5-d]pyrimidine-2,7-dione (2), 3-phenylthiazolo[4,5-d]pyrimidine-2,7(6H)-dione (3) and/or 5-N-methylcarbamoyl-3-phenyl-2,4-thiazolidinedione (5), depending on reaction conditions. Furthermore, reaction of 3 with dimethyl sulfate caused the ring opening to give corresponding 5. Also, treatment of 5 with phosphorus oxychloride gave 4-chloro-2-oxo-3-phenylthiazolidine-5-N-methylcarboxamide (6).