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The synthesis and some reactions of 2‐methyl‐4,5‐pyrimidinediearbonitrile
Author(s) -
Schwan Thomas J.,
Tieckelmann Howard
Publication year - 1965
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.5570020218
Subject(s) - chemistry , nucleophile , methanol , dimethylformamide , pyrimidine , medicinal chemistry , organic chemistry , catalysis , stereochemistry , solvent
Diethyl ethoxymethyleneoxalacetate and acetamidine gave 2‐methyl‐4,5‐bis(carbethoxy)‐pyrimidine. The ester was converted to 2‐methyl‐4, 5‐pyrimidinedicarbonitrile which gave 2‐methyl‐4‐methoxy‐5‐pyrimidinecarbonitrile when treated with methanol at room temperature. Attempts to hydrogenate the dinitrile in the presence of nucleophiles led to displacement at C‐4. Attempted hydrogenation of the dinitrile in dimethylformamide gave 2,2′‐dimethyl‐5, 5′‐dicyano‐4, 4′‐bipyrimidine.