Ruben S Vardanyan1, Gevork G Danagulyan2, Armen D Mkrtchyan2, Victor J Hruby1. 1. Departments of Chemistry and Biochemistry, 1306 University Boulevard, University of Arizona, Tucson, AZ 85721, USA. 2. Russian-Armenian (Slavonic) State University, 123 H. Emin Street, Yerevan 375051, Republic of Armenia.
Abstract
The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (3) with alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde (5). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C-C recyclizations: 2-benzyl-4-benzylamino-5-carbamoylpyrimidine (7) and the benzylimine of 4-amino-2-benzyl-6-benzylaminopyrimidine-5-carbaldehyde (8). The reaction of 2-amino-1,4-dimethyl-5-ethoxycarbonylpyrimidinium iodide (10) with KOH ethanolic solution gave a single product of C-C-recyclization: 2-amino-5-acetyl-4-hydroxypyrimidine (11).
The reaction of 4-amino-2-benzyl-1-methyl-5-ethoxycarbonylpyrimidinium iodide (3) with n class="Chemical">alcoholic methylamine resulted in the formation of the methylimine of 2-amino-4-hydroxy-6-methylamino-5-phenylpyridine-3-carbaldehyde (5). Heating of the same pyrimidinium salt in benzylamine gave a mixture of products of two C-C recyclizations: 2-benzyl-4-benzylamino-5-carbamoylpyrimidine (7) and the benzylimine of 4-amino-2-benzyl-6-benzylaminopyrimidine-5-carbaldehyde (8). The reaction of 2-amino-1,4-dimethyl-5-ethoxycarbonylpyrimidinium iodide (10) with KOH ethanolic solution gave a single product of C-C-recyclization: 2-amino-5-acetyl-4-hydroxypyrimidine (11).
Authors: E Nicolaï; G Curé; J Goyard; M Kirchner; J M Teulon; A Versigny; M Cazes; F Caussade; A Virone-Oddos; A Cloarec Journal: J Med Chem Date: 1994-07-22 Impact factor: 7.446
Authors: N Suzuki; T Miwa; S Aibara; H Kanno; H Takamori; M Tsubokawa; Y Ryokawa; W Tsukada; S Isoda Journal: Chem Pharm Bull (Tokyo) Date: 1992-02 Impact factor: 1.645