Journal of Medicinal Chemistry p. 535 - 541 (1980)
Update date:2022-09-26
Topics:
Roth, Barbara
Aig, Edward
Lane, Kenneth
Rauckman, Barbara S.
The preparation of a wide variety of 6-substituted trimethoprim analogues was readily accomplished by the reaction of 2,4-diamino-6-substituted-pyrimidines with 2,6-dimethoxy-4-<(N,N-dimethylamino)methyl>phenol at 120-160 deg C.The less reactive 2,6-dialkyl-4-<(N,N-dimethylamino)methyl>phenols reacted successfully with 2,4-diamino-6-(alkylthio)pyrimidines to give 5-(substituted benzyl)pyrimidines.The phenolic groups of the products were alkylated in high yield when a nonreactive 6-substituent was present in the pyrimidine ring. 6-(Alkylthio) groups were easily removed with Raney nickel.Trimethoprim was thus obtained in high yield from its 6-(methylthio) counterpart.The 6-substituted trimethoprim analogues all had low activity as inhibitors of Escherichia coli dihydrofolate reductase and as antibacterial agents.
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