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An improved procedure for the preparation of 2‐amino‐8‐alkylpyrido‐[2,3‐ d ]pyrimidin‐4(3 H )‐ones (8‐alkyl‐N5‐deazapterins)
Author(s) -
Ivery Michael T. G.,
Gready Jill E.
Publication year - 1994
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.5570310615
Subject(s) - chemistry , alkyl , yield (engineering) , medicinal chemistry , organic chemistry , metallurgy , materials science
We report an improved procedure for the preparation of 8‐alkyl‐N5‐deazapterins which allows clean preparation of all ring‐methyl substituted compounds, including 5‐ and 7‐methyl substituted compounds. The procedure was also successfully applied to the preparation of N5‐deazapterins with improved yield over previous reports. The uv/visible and p K a data confirm the predicted increased basicity of 8‐alkyl‐N5‐deazapterins compared with the N5‐deazapterin parents, and indicate that N5‐deazapterins protonate on N8 and 8‐alkyl‐N5‐deazapterins protonate on N3.