Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1998-11-13
2000-07-11
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
C07D23928, C07D23930
Patent
active
060875003
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to methods for producing 2-amino-4,6-dimethoxypyrimidine useful as an intermediate for drugs and pesticides, particularly as an intermediate for herbicides, its starting material 2-amino-5-chloro-4,6-dimethoxypyrimidine and its intermediate 2-amino-4,5-dichloro-6-methoxypyrimidine.
BACKGROUND ART
2-Amino-4,6-dimethoxypyrimidine and its derivatives are a group of compounds which are useful as intermediates for various fine chemicals such as biologically active substances, like drugs and pesticides as well as important intermediates for sulfonylurea herbicides described in JP-A-59-122488, JP-A-61-210084 and JP-A-60-208977.
2-Amino-4,5-dichloro-6-methoxypyrimidine is useful, for example, for producing phenylaminopyrimidine compounds described in JP-A-60-51177 and JP-A-61-15877.
As a method for producing 2-amino-4,6-dimethoxypyrimidine, many methods have been known. For example, JP-B-1-211411 discloses a production method by reacting bisimidate obtained from malononitrile with cyanogenchloride. And JP-A-64-16770 discloses a method for producing 2-amino-4,6-dimethoxypyrimidine by reacting 2-amino-4,6-dihydroxypyrimidine with phosphorous oxychloride in the presence of an organic base to prepare 2-amino-4,6-dichloropyrimidine (J. Amer. Chem. Soc., vol. 73, page 3011 (1951)), followed by methoxylation with a metal hydroxide and methanol.
On the other hand, as a method for producing 2-amino-5-chloro-4,6-dimethoxypyrimidine, a method to chlorinate 2-amino-4,6-dimethoxypyrimidine has been known as described in J. Chem. Soc. Perkin Trans. 1, page 375 (1975).
However, with the conventional methods, various types of by-products are generated with large quantities, and improvement is therefore required. And, 2-amino-4,5-dichloro-6-methoxypyrimidine and methods for its production have not been known at all.
DISCLOSURE OF THE INVENTION
The present inventors have conducted extensive studies to overcome the above problems, and the present invention has been accomplished. Namely, the present invention provides a method for producing 2-amino-4,6-dimethoxypyrimidine (hereinafter referred to as compound (I)), characterized by reacting 2-amino-5-chloro-4,6-dimethoxypyrimidine (hereinafter referred to as compound (II)) with a hydrogen donor using a metal catalyst selected from nickel catalyst, palladium catalyst and platinum catalyst, in the presence of a base if necessary (hereinafter referred to as production method A), a method for producing compound (I), using compound (II) produced by reacting 1,1,1,2,2,3,3-heptachloropropane, 1,1,1,2,3,3,3-heptachloropropane or hexachloropropene with guanidine or its salt, in the presence of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal methoxide or an alkaline earth metal methoxide (hereinafter referred to as production method A1), a method for producing compound (I), using compound (II) produced by reacting 2-amino-4,5-dichloro-6-methoxypyrimidine (hereinafter referred to as compound (III)) with methanol, in the presence of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal methoxide or an alkaline earth metal methoxide (hereinafter referred to as production method A2), a method for producing compound (II), using compound (III) produced by reacting 2-amino-4,5,6-trichloropyrimidine (hereinafter referred to as compound (IV)) with methanol, in the presence of an alkali metal carbonate, an alkali metal hydrogencarbonate, an alkaline earth metal carbonate or an alkaline earth metal hydrogencarbonate (hereinafter referred to as production method A3), a method for producing compound (I), using compound (II) produced by reacting compound (IV), with methanol, in the presence of an alkali metal hydroxide, an alkaline earth metal hydroxide, an alkali metal methoxide or an alkaline earth metal methoxide (hereinafter referred to as production method A4), a method for producing compound (I), characterized by reacting 1,1,1,3,3,3-hexachloropropane or 1,1,3,3,3-pentachloropropene with guanidine
REFERENCES:
Baldwin et al. Condenstion reaction of chloroformylsulfur . . . J. Chem. Soc. Perkins Trans. 375-377, 1975.
Fukuda Kenzo
Hatanaka Masataka
Ishii Kenichi
Makabe Takahiro
Balasubramanian Venkataraman
Nissan Chemical Industries Ltd.
Shah Mukund J.
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