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Chemistry of 5‐pyrimidinecarboxaldehydes
Author(s) -
Bell Lawrence,
McGuire H. Michael,
Freeman G. Andrew
Publication year - 1983
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.5570200110
Subject(s) - chemistry , hydrolysis , oxime , amino acid , stereochemistry , medicinal chemistry , organic chemistry , biochemistry
Selective hydrolysis of 2‐amino‐4,6‐dichloro‐5‐pyrimidinecarboxaldehyde, 2 , gave 2‐amino‐4‐chloro‐1,6‐dihydro‐6‐oxo‐5‐pyrimidinecarboxaldehyde, 5 . The oxime of 2 rearranged to 2‐amino‐4‐chloro‐1,6‐dihydro‐6‐oxo‐5‐pyrimidinecarbonitrile, 8 . Reaction of 8 with 4‐phenylbutylamine resulted in the displacement of the 4‐chloro atom to give compound 9 . Hydrolysis of the cyano function of 9 gave amides 12 , 13 , and 14 depending on reaction conditions. A discussion of the 1H‐nmr spectrum of 2‐amino‐1,6‐dihydro‐6‐oxo‐4‐[(4‐phenylbutyl)amino]‐5‐ pyrimidinecarboxaldehyde, 6 , is presented.