39800-76-5Relevant academic research and scientific papers
Syntheses of Antibacterial 2,4-Diamino-5-benzylpyrimidines. Ormetoprim and Trimethoprim
Manchand, Percy S.,Rosen, Perry,Belica, Peter S.,Oliva, Gloria V.,Perrotta, Agostino V.,Wong, Harry S.
, p. 3531 - 3535 (2007/10/02)
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 75percent 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. 12 was prepared from 3-bromo-4-methoxytoluene by a Cu(I)-catalyzed displacement of bromine by methoxide and 4,5-dimethoxy-2-methylbenzaldehyde was obtained from 12 in 87percent yield by a pyridine-catalyzed Vilsmeier reaction using DMF-POCl3.
Process for substituted 5-benzyl-2,4-diamino-pyrimidines
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, (2008/06/13)
A process for preparing a compound of the formula STR1 wherein R1 and R2 are lower alkoxy or taken together are METHYLENEDIOXY; R3 is lower alkyl or hydrogen, which comprises the step of reacting an aromatic compound of the formula STR2 wherein R1, R2 and R3 are as previously described, with a diamino-pyrimidine of the formula STR3 wherein R4 is lower alkoxy, benzyloxy, hydroxy or halogen, in the presence of an inorganic or organic acid selected from the group consisting of ortho-phosphoric acid, poly-phosphoric acid, hydrohalic acids and tri-haloacetic acids, at a temperature in the range of from about 50° C. to about 110° C., is described.
