Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Reexamination Certificate
2000-08-30
2002-01-22
Ford, John M. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
C504S136000
Reexamination Certificate
active
06340757
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to a 6-(1-fluoroalkyl)-4-pyrimidone and processes for producing the same, more specifically, to a novel 6-(1-fluoroalkyl)-4-pyrimidone which is important as a synthetic intermediate of aminopyrimidine derivatives which are useful as acaricides, fungicides and nematocides, and processes for producing the same.
FIELD OF THE INVENTION
Aminopyrimidine derivatives useful as insecticides, acaricides, fungicides or nematocides have been described, for example, in Japanese Provisional Patent Publications No. 230036/1993, No. 25187/1994, No. 116247/1994, No. 247939/1994, No. 258223/1995, etc. However, the synthetic intermediates of the present invention have not yet been known as synthetic intermediates for the aminopyrimidine derivatives, and thus, the process for producing the same has not yet been known.
The present invention provides a novel 6-(1-fluoroalkyl)-4-pyrimidone which is important as a synthetic intermediate and a process for producing the same.
The present invention solves the above-mentioned problems, and as a result, 6-(1-fluoroalkyl)-4-pyrimidone which is a novel compound can be an important intermediate of the above-mentioned useful aminopyrimidine derivatives. A process for producing 6-(1-fluoroalkyl)-4-pyrimidone is also set forth.
SUMMARY OF THE INVENTION
The first aspect of the present invention relates to 6-(1-fluoroalkyl)-4-pyrimidones represented by the following formula (1):
wherein R
1
represents an alkyl group; R
2
represents a hydrogen atom or an alkyl group; and R
3
represents a hydrogen atom, an alkyl group or a chlorine atom.
The second aspect of the invention relates to a process for producing 6-(1-fluoroalkyl)-4-pyrimidones represented by the following formula (1-A):
wherein R
1
and R
2
have the same meanings as defined above; and R
3
′ represents a hydrogen atom or an alkyl group,
which comprises allowing a 4-fluoro-3-oxocarboxylate represented by the following formula (2):
wherein R
1
, R
2
and R
3
′ have the same meanings as defined above; and
R
4
represents an alkyl group,
to react with formamidine in the presence of a base.
The third aspect of the invention relates to a process for producing 5-chloro-6-(1-fluoroalkyl)-4-pyrimidones represented by the following formula (1-B):
wherein R
1
and R
2
have the same meanings as defined above, which comprises subjecting 6-(1-fluoroalkyl)-4-pyrimidone represented by the following formula (1-A′):
wherein R
1
and R
2
have the same meanings as defined above, to chlorination reaction with a chlorinating agent.
DETAILED DESCRIPTION OF THE INVENTION
In the following, the present invention will be explained in more detail.
R
1
to R
4
in the above-mentioned formula (1) are as mentioned below.
R
1
to R
4
in 6-(1-fluoroalkyl)-4-pyrimidone (Compound (1)) which is represented by the above-mentioned formula (1) which is a compound of the present invention and in 4-fluoro-3-oxocarboxylate (Compound (2)) represented by formula (2) which is a starting material, are as mentioned below.
R
1
is a straight or branched alkyl group.
The alkyl group in R
1
has 1 to 10 carbon atoms, preferably 1 to 4.
R
2
is a hydrogen atom, or a straight or branched alkyl group.
R
3
is a hydrogen atom, a straight or branched alkyl group or a chlorine atom.
R
3
′ is a hydrogen atom or a straight or branched alkyl group.
The alkyl group in R
2,
R
3
and R
3
′ has 1 to 10 carbon atoms, preferably 1 to 4, and more preferably a methyl group.
R
4
is a straight or branched alkyl group.
The alkyl group in R
4
has 1 to 10 carbon atoms, preferably 1 to 4.
The compound (1) of the present invention is exemplified below.
6-(1-Fluoroethyl)-4-pyrimidone,
6-(1-Fluoro-1-methylethyl)-4-pyrimidone,
6-(1-Fluoropropyl)-4-pyrimidone,
6-(1-Fluoro-1-methylpropyl)-4-pyrimidone,
6-(1-Fluorobutyl)-4-pyrimidone,
6-(1-Fluoro-1-methylbutyl)-4-pyrimidone,
6-(1-Fluoropentyl)-4-pyrimidone,
6-(1-Fluoro-1-methylpentyl)-4-pyrimidone,
6-(1-Fluoroethyl)-5-methyl-4-pyrimidone,
6-(1-Fluoro-1-methylethyl)-5-methyl-4-pyrimidone,
6-(1-Fluoropropyl)-5-methyl-4-pyrimidone,
6-(1-Fluoro-1-methylpropyl)-5-methyl-4-pyrimidone,
6-(1-Fluorobutyl)-5-methyl-4-pyrimidone,
6-(1-Fluoro-1-methylbutyl)-5-methyl-4-pyrimidone,
6-(1-Fluoropentyl)-5-methyl-4-pyrimidone,
6-(1-Fluoro-1-methylpentyl)-5-methyl-4-pyrimidone,
5-Chloro-6-(1-fluoroethyl)-4-pyrimidone,
5-Chloro-6-(1-fluoro-1-methylethyl)-4-pyrimidone,
5-Chloro-6-(1-fluoropropyl)-4-pyrimidone,
5-Chloro-6-(1-fluoro-1-methylpropyl)-4-pyrimidone,
5-Chloro-6-(1-fluorobutyl)-4-pyrimidone,
5-Chloro-6-(1-fluoro-1-methylbutyl)-4-pyrimidone,
5-Chloro-6-(1-fluoropentyl)-4-pyrimidone,
5-Chloro-6-(1-fluoro-1-methylpentyl)-4-pyrimidone,
and the like.
The compound (2) which is a starting material to be used in the present invention can be easily obtained from a carboxylate
Formamidine to be used in the present invention may be used in the form of a salt, for example, an acetate, a hydrochloride, a sulfate, etc., of formamidine.
An amount of the formamidine salt to be used is preferably 1-fold mole or more, more preferably 1- to 3-fold mole based on the amount of the compound (2).
The base to be used is preferably an alkali metal alkoxide such as sodium methoxide, sodium ethoxide, sodium butoxide, potassium t-butoxide, etc.
An amount of the base to be used is preferably 1-fold mole or more, more preferably 1- to 3-fold mole based on the amount of the formamidine salt.
Synthesis of the compound (1-A) may be carried out without using any solvent, and when a solvent is used, it is not particularly limited so long as it does not participate in the present reaction. There may be mentioned, for example, an alcohol such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, etc., an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, etc., an ether such as tetrahydrofuran, dimethoxyethane, etc. Also, these solvents may be used singly or in admixture.
An amount of the solvent to be used is preferably 1- to 50-fold volume, more preferably 2- to 30-fold volume based on the amount of the compound (2).
In the synthesis of the compound (1-A), a reaction temperature to be employed is preferably −10 to 100° C., more preferably 0 to 70° C.
A reaction time in the synthesis of the compound (1-A) may vary depending on the concentration, temperature and amounts to be used, but generally is 0.5 to 15 hours.
The chlorinating agent to be used in the present invention is preferably a chlorine and sulfuryl chloride.
An amount of the chlorinating agent to be used in the present invention is preferably 0.9-fold mole or more, more preferably 0.9 to 4.0-fold mole based on the amount of the compound (1-A′).
In the synthesis of the compound (1-B), a solvent may be used or may not be used, and when a solvent is used, it is not particularly limited so long as it does not participate in the present reaction. For example, an aliphatic halogenated hydrocarbon such as dichloromethane, chloroform, dichloroethane, etc., an aromatic halogenated hydrocarbon such as chlorobenzene, etc., an amide such as N,N-dimethylformamide, N,N-dimethylacetamide, etc., an ether such as diethyl ether, tetrahydrofuran, dimethoxyethane, etc. may be used singly or in admixture.
An amount of the solvent to be used is preferably 0- to 50-fold volume, more preferably 2- to 30-fold volume based on the amount of the compound (1-A′).
In the synthesis of the compound (1-B) of the present invention, a reaction temperature to be employed is preferably −10 to 100° C., more preferably −5 to 70° C.
A reaction time in the synthesis of the compound (1-B) of the present invention may vary depending on the concentration, temperature and amounts to be used, but is generally 0.5 to 10 hours.
The compound (1) of the present invention prepared as mentioned above may be subjected to post-treatments such as washing, extraction, concentration, etc., after completion of the reaction, and may be purified by conventionally known means such as recrystallization, various kinds of chromatography, etc., de
Fuse Kensaku
Morita Kazuhiro
Ohmori Kiyoshi
Onduka Yoshitaka
Yokota Naoyuki
Ford John M.
Jordan and Hamburg LLP
Truong Tamthom N.
Ube Industries Ltd.
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