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The preparation of pyrimidine analogs of the 2,6-di-tert-butylphenol antiinflammatory agents Prifelone (R-830), Tebufelone (NE-11740) and Ym-13,162 is described. Grignard addition to the N-methoxy-N-methylamide derived from 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinecarboxylic acid yielded a series of 2-pyrimidinyl ketones. Further elaboration of an ethyl ketone and cyclization with sodium cyanate gave a pyrimidinylimidazole.

Improved processes for the synthesis of bulk quantities of the anthrapyrazole clinical agents CI-937, CI-941, and piroxantrone hydrochloride are reported. Reported also are detailed analytical and spectroscopic data for these agents and intermediates of the synthetic sequences.

Reaction of the nitrothioxanthen-9-ones (I) with the aminoalkylhydrazine (II) gives the 5-nitrobenzothiopyranoindazoles (III) which are reduced, forming the corresponding amino compounds (IV).

Improved processes for the synthesis of bulk quantities of the anthrapyrazole clinical agents CI-937, CI-941, and piroxantrone hydrochloride are reported. Reported also are detailed analytical and spectroscopic data for these agents and intermediates of the synthetic sequences.