Paper
The Reaction of Methyl 2-Dimethoxymethyl-3-methoxypropionate with Amidines
Published Feb 1, 1973 · Takenori Nishino, Yoshiyuki Miichi, K. Tokuyama
Bulletin of the Chemical Society of Japan
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Abstract
The reaction of methyl 2-dialkoxymethyl-3-methoxypropionate with acetamidine has been reported to afford 2-methyl-4-hydroxy-5-methoxymethylpyriniidine (13a) by a different mode than the reaction of 2-dimethoxy-methyl-3-methoxypropionitrile (1), which affords dihydropyrimidopyrimidine (4). As the presence of this difference seemed to be somewhat curious from the viewpoint of the reaction mechanism, the reaction of methyl 2-dimethoxymethyl-3-methoxypropionate (7) with acetamidine was reinvestigated. The reaction products were 13a and acetamidinomethylpyrimidine (17a). Similar results were obtained by the reaction of 7 with benzamidine. As the compound 17 corresponds to 4, the reaction of 7 was concluded to proceed in a manner similar to that of 1; that is, no essential difference exists between the reactions of 1 and 7 with amidines.
The reaction of methyl 2-dimethoxymethyl-3-methoxypropionate with acetamidine is similar to that of 2-dimethoxy-methyl-3-methoxypropionitrile, yielding 13a and acetamidinomethylpyrimidine (17a).
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