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Synthese von zwei Metaboliten des 2,4‐Diamino‐5‐(3,4,5‐tri‐methoxybenzyl)‐pyrimidins (Trimethoprim)
Author(s) -
ReyBellet G.,
Reiner R.
Publication year - 1970
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19700530509
Subject(s) - chemistry , hydrogenolysis , metabolite , trimethoprim , pyrimidine , guanidine , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry , antibiotics
The synthesis of two metabolites M 3 and M 4 of 2,4‐diamino‐5‐(3, 4, 5‐trimethoxybenzyl)‐pyrimidine (trimethoprim, 1 ) is reported. M 3 (trimethoprim 1‐oxide) as well as the isomeric 3‐oxide were prepared by oxidation of 1 with m ‐chloroperbenzoic acid. The structure of M 3 was finally established by x ‐ra analysis [4]. The metabolite M 4 [2, 4‐diamino‐5‐(3‐hydroxy‐4, 5‐dimethoxy‐benzyl)‐pyrimidine] was prepared by condensation of 3‐benzyloxy‐4, 5‐dimethoxybenzaldehyde ( 2 ) with 3‐methoxypropionitrile ( 3 ) and guanidine followed by hydrogenolysis of the intermediate 3‐benzyloxy compound 4 .