ChemInform Abstract: Syntheses of Antibacterial 2,4-Diamino-5-benzylpyrimidines. Ormetoprim and Trimethoprim

Autor:	Perry Rosen, Agostino Perrotta, Percy S. Manchand, Peter S. Belica, Gloria Oliva, Harry S. Wong
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Ormetoprim Chemistry Yield (chemistry) medicine Substrate (chemistry) General Medicine Guanidine Medicinal chemistry Combinatorial chemistry Trimethoprim Isomerization medicine.drug
Zdroj:	ChemInform. 23
ISSN:	0931-7597
DOI:	10.1002/chin.199246183
Popis:	A general and mild method for the synthesis of 2,4-diamino-5-benzylpyrimidines was achieved by the Friedel-Crafts reaction between 2-(methoxymethylene)-3-methoxypropanenitrile (10) and an activated aromatic substrate followed by treatment with guanidine. The method is illustrated by a synthesis of ormetoprim (2) in 75% overall yield from 3,4-dimethoxytoluene (12). Efficient syntheses of trimethoprim (1) and 2 were also accomplished via prior base-catalyzed 1,3-prototropic isomerization of cinnamonitriles 19 and 20, respectively, followed by condensation with guanidine
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f41ab6e943342faf06d2bff51b5d3621 https://doi.org/10.1002/chin.199246183 Zobrazit plný text záznamu Plný text