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Synthesis of pyrimidine analogs of 2,6‐Di‐ tert ‐butylphenol antiinflammatory agents
Author(s) -
Unangst Paul C.,
Connor David T.,
Kostlan Catherine R.,
Shrum Gary P.,
Miller Steven R.,
Kanter Gerald
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320417
Subject(s) - chemistry , pyrimidine , ketone , medicinal chemistry , stereochemistry , organic chemistry
Abstract 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.