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Synlett 1990; 1990(10): 577-578
DOI: 10.1055/s-1990-21170
DOI: 10.1055/s-1990-21170
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A Simple Synthesis of 5,8,10-Trideazaminopterin Analogues
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Publication History
Publication Date:
08 March 2002 (online)
The Heck reaction between 2,4-diamino-6-iodoquinazoline and methyl 4-ethynylbenzoate gives 2,4-diamino-6-[(4-methoxycarbonylphenyl)ethynyl] quinazoline in high yield. This intermediate may be converted by a series of simple transformations into 5,8,10-trideazaminopterin, the quinazoline analogue of 10-deazaminopterin. Alternatively, the acetylene may be elaborated to give N-{4-[(Z)-2-(2,4-diamino-6-quinazolinyl)-ethenyl]benzoyl}-L-glutamic acid, the first example of a conformationally restricted 10-deazaminopterin analogue.