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Synthesis of some new thieno[3,4‐ d ]pyrimidines and their C ‐nucleosides
Author(s) -
Patil Shirish A.,
Otter Brian A.,
Klein Robert S.
Publication year - 1993
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570300240
Subject(s) - chemistry , stereochemistry , pyrimidine , nucleoside , nitromethane , derivative (finance) , thio , bicyclic molecule , carboxylate , thiophene , yield (engineering) , organic chemistry , financial economics , economics , metallurgy , materials science
The synthesis of several new thieno[3,4‐ d ]pyrimidine C ‐nucleosides 5‐8 is described. The known 5‐ribosyl‐ated methyl 4‐(formylamino)thiophene‐3‐carboxylate key intermediate 20 was obtained as a mixture of anomers in significantly improved yield by condensation of the sugar 15 with methyl 4‐(formylamino)thio‐phene‐3‐carboxylate 19 in nitromethane at 60° in the presence of stannic chloride. Attempts to prepare the C‐7 ribosylated compound 21 β by direct condensation of the bicyclic base 10 with 15 gave instead the N‐1 ribosylated nucleoside 16 . The synthesis of the corresponding and previously unknown thieno[3,4‐ d ]pyrimi‐dine bases 12 and 13 is described along with stability studies on the 4‐methylthio derivative 12 . Preliminary biological studies indicate that adenosine analogue 7 is a potent growth inhibitor of several mammalian tumor cell lines.