Improved syntheses in the pyrimidine series. IV. N‐methyl derivatives of 4: 5‐diaminopyrimidine
- 1 August 1955
- journal article
- research article
- Published by Wiley in Journal of Chemical Technology & Biotechnology
- Vol. 5 (8) , 358-364
- https://doi.org/10.1002/jctb.5010050802
Abstract
4‐Amino‐5‐methylaminopyrimidine has been synthesized by reduction with lithium aluminium hydride of the formyl group in 4‐amino‐5‐formamido‐2‐methylthiopyrimidine followed by removal of the 2‐substituent. A route to 5‐amino‐4‐hydroxy‐6‐methylaminopyrimidine is described. The Whitehead synthesis has been extended to the use of cyanoacetic acid as a reactant. Decarboxylation of the resulting 4‐amino‐5‐carboxy‐3‐methyl‐2‐pyrimidone, however, gave unexpectedly 2‐hydroxy‐4‐methylaminopyrimidine. Several improvements in the preparation of known related (methylated) compounds, including the first isolation of 5‐amino‐1‐methyl‐4‐methylamino‐2‐pyrimidone are described.Keywords
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