Highly Selective Hydrolysis of Chloropyrimidines to Pyrimidones in 12 N Hydrochloric Acid

2006 ◽  
Vol 10 (5) ◽  
pp. 921-926 ◽  
Author(s):  
Amphlett G. Padilla ◽  
Bruce A. Pearlman
1974 ◽  
Vol 27 (8) ◽  
pp. 1781 ◽  
Author(s):  
DJ Brown ◽  
RK Lynn

Syntheses of hitherto unknown 3-aminopyrimido[5,4-e]-as-triazin-5-ones are described. One route involves selective hydrolysis of 3,5-di- or 3,5,7-tri-alkoxypyrimidotriazines at the 5-position followed by aminolysis. Another is exemplified thus: 3-ethoxy-5-methoxypyrimidotriazine (2a) is converted by methanolic hydrochloric acid into methyl 6-amino-3-ethoxy-1,2,4-triazine-5-carboxylate (3a) which then undergoes successive ammonolysis to the corresponding amide (3b), cyclization by triethyl orthoformate-acetic anhydride to 3-ethoxypyrimidotriazin-5-one (1d) and final ammonolysis to the corresponding amine (1a). The second route may be modified to furnish 3-aminopyrimidotriazine- 5,7-dione (5c) and its 6-methyl derivative (5d). Dehydration of the above amide (3b) with phosphoryl chloride gives both the corresponding nitrile (3h) and an unusual hydrolytic product, 6-amino-3- ethoxytriazin-5-one (6). The ionization constants and the u.v., N.M.R. and mass spectra are discussed.


2014 ◽  
Vol 11 (6) ◽  
pp. 684-689 ◽  
Author(s):  
Jing-Yuan LIU ◽  
He-Shui YU ◽  
Bing FENG ◽  
Li-Ping KANG ◽  
Xu PANG ◽  
...  

1997 ◽  
Vol 38 (17) ◽  
pp. 2981-2984 ◽  
Author(s):  
Véronique Le Boisselier ◽  
Michèle Postel ◽  
Elisabet Duñach

1983 ◽  
Vol 23 (5) ◽  
pp. 471 ◽  
Author(s):  
A. Haas ◽  
W. Wanzke ◽  
N. Welcman

Holzforschung ◽  
1981 ◽  
Vol 35 (6) ◽  
pp. 283-286 ◽  
Author(s):  
John Papadopoulos ◽  
Chen-Loung Chen ◽  
Irving S. Goldstein

ChemInform ◽  
2010 ◽  
Vol 42 (2) ◽  
pp. no-no
Author(s):  
Purba Mukerjee ◽  
Mohammed Abid ◽  
Frank C. Schroeder

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