CN104326989B - The preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine - Google Patents

The preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine Download PDF

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CN104326989B
CN104326989B CN201410696621.8A CN201410696621A CN104326989B CN 104326989 B CN104326989 B CN 104326989B CN 201410696621 A CN201410696621 A CN 201410696621A CN 104326989 B CN104326989 B CN 104326989B
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methyl
amino
pyrimidine
methane amide
alkaline agent
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CN104326989A (en
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章根宝
司玉贵
郭军
万真
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JIANGXI TIANXIN PHARMACEUTICAL Co.,Ltd.
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JIANGXI TIANXIN PHARMACEUTICAL CO Ltd
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    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/582Recycling of unreacted starting or intermediate materials

Abstract

The invention discloses a kind of preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine, it is characterized in that, the method comprises: under the existence of alkaline agent, 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol are carried out contact reacts, and the weight ratio of the consumption of described alkaline agent and the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine is 0.001-0.05:1.According to method provided by the invention, can not produce a large amount of organic salt, inorganic salt and waste liquid, and by product and residue methyl alcohol can all recyclings, the method economy, environmental protection, meet the demand for development of current national energy-conserving and environment-protective industrial economy.In addition, preparation method provided by the invention, simple to operate, raw material is easy to get and product is easy to separation and purification, is applicable to the requirement of suitability for industrialized production.

Description

The preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine
Technical field
The present invention relates to a kind of preparation method of intermediate of VITMAIN B1, particularly, relate to a kind of preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine.
Background technology
VITMAIN B1 is as a kind of important basal nutrient composition, and have multiple important physiological action, its preparation method receives much concern always.2-methyl-4-amino-5-(amino methyl) pyrimidine (GDA) also receives as a kind of key intermediate preparing VITMAIN B1 and pays close attention to widely, its English name is: 2-methyl-4-amino-5-(aminomethyl) pyrimidine, and its structural formula is as follows:
At present, under the effort of at home and abroad chemist, define the route approach of number of chemical synthesise vitamins B1, wherein, also be proved to be most economical the most effective by the technique of preferentially synthesizing this key intermediate of GDA, manufacturing enterprise all adopts by the method being finally prepared into VITMAIN B1 after synthesis GDA more both at home and abroad at present.But, these methods are generally be hydrolyzed in the aqueous solution of alkali by intermediate 2-methyl-4-amino-5-(methane amide methyl) pyrimidine to obtain GDA, a large amount of organic salt and inorganic salt and waste water can be produced, both caused the waste of resource, and also can cause environmental issue and add the cost of wastewater treatment.
Therefore, in order to adapt to the requirement of Current resource intense situation and environmental protection, this area is needed a kind of economic environmental protection of exploitation badly and is applicable to the GDA preparation method of suitability for industrialized production.
Summary of the invention
The object of the invention is to overcome in the preparation method of existing 2-methyl-4-amino-5-(amino methyl) pyrimidine and produce a large amount of salt and the uneconomical and defect not environmentally of waste liquid, a kind of economy, environmental protection and be applicable to the preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine of suitability for industrialized production are provided.
The present inventor finds under study for action; by 2-methyl-4-amino-5-(carbamoylmethyl) pyrimidine and methyl alcohol are carried out contact reacts under the catalysis of a small amount of alkaline agent; can prepare 2-methyl-4-amino-5-(amino methyl) pyrimidine when not producing a large amount of organic salt, inorganic salt and waste liquid, and gained by product and remaining methanol solution can reclaim realization recycling.
To achieve these goals, the invention provides a kind of preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine, wherein, the method comprises: under the existence of alkaline agent, 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol are carried out contact reacts, and the weight ratio of the consumption of described alkaline agent and the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine is 0.001-0.05:1.
The preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine provided by the invention, a large amount of organic salt, inorganic salt and waste liquid can not be produced, and by product and residue methyl alcohol can all recyclings, the method economy, environmental protection, meet the demand for development of current national energy-conserving and environment-protective industrial economy.In addition, preparation method provided by the invention, simple to operate, raw material is easy to get and product is easy to separation and purification, is applicable to the requirement of suitability for industrialized production.
Other features and advantages of the present invention are described in detail in embodiment part subsequently.
Embodiment
Below the specific embodiment of the present invention is described in detail.Should be understood that, embodiment described herein, only for instruction and explanation of the present invention, is not limited to the present invention.
The invention provides a kind of preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine, wherein, the method comprises: under the existence of alkaline agent, 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol are carried out contact reacts, and the weight ratio of the consumption of described alkaline agent and the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine is 0.001-0.05:1.
According to method provided by the invention, all there is no particular limitation for the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol, under preferable case, the mol ratio of the described consumption of 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and the consumption of described methyl alcohol is 1:1-100, under further preferable case, the mol ratio of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and described methyl alcohol is 1:20-40.
According to method provided by the invention, described alkaline agent is used for the reaction of catalysis 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol, the consumption of described alkaline agent is crossed and is made reaction abundant not at least, consumption crosses the decline that can cause product purity at most, therefore, under preferable case, the weight ratio of the consumption of described alkaline agent and the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine is 0.005-0.02:1.
In the present invention, described alkaline agent is not particularly limited, can be the alkaline agent that this area routine uses, such as described alkaline agent be one or more in sodium hydroxide, sodium methylate, sodium ethylate, ethamine, diethylamine, triethylamine, methylamine, dimethylamine and ammonia.When described alkaline agent is ammonia, the consumption of described alkaline agent refers to the meltage of ammonia in methyl alcohol.Under preferable case, described alkaline agent is one or more in sodium methylate, sodium ethylate and triethylamine; Under further preferable case, described alkaline agent is sodium methylate.
According to method provided by the invention, in order to promote fully carrying out of reaction further, under preferable case, described catalytic condition comprises: temperature of reaction is 60-150 DEG C, and the reaction times is 1-30 hour.Under further preferable case, described catalytic condition comprises: temperature of reaction is 90-120 DEG C, and the reaction times is 2-10 hour.
According to method provided by the invention, under preferable case, described contact reacts is carried out in encloses container.In the present invention, because reaction can cause reaction system pressure to raise, under preferable case, described encloses container is the reaction vessel that can bear pressure, and such as described encloses container can be autoclave.Volume for described encloses container is not particularly limited, and those skilled in the art can select arbitrarily according to actual needs.
In order to promote the abundant reaction of 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol further, described contact reacts can under agitation be carried out, the method of described stirring can be the method that this area routine uses, such as mechanical stirring and magnetic agitation.
According to method provided by the invention, the step that the method is carried out solid-liquid separation and described solid-liquid separation gained filtrate concentrated after can also comprising the mixture cooling obtained 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol contact reacts.
According to method provided by the invention, the mixture that described cooling makes contact reacts obtain is cooled to less than 50 DEG C, and described cooling is not particularly limited, and the method for such as described cooling can be naturally cooling or ice bath cooling.
According to method provided by the invention, the method for described solid-liquid separation is not particularly limited, and can be the various solid-liquid separating methods that this area routine uses, such as centrifugation, suction filtration etc.
According to method provided by the invention, for described concentrated method, also there is no particular limitation, such as, can be the various distillating methods that this area routine uses, such as air distillation, underpressure distillation etc.
In the present invention, in described concentration process, different according to boiling point, the recovery of byproduct formic acid methyl esters and methyl alcohol can be realized, the methyl alcohol reclaimed can realize the recycling of producing, and methyl-formiate is as a kind of very useful chemical reagent, such as, can recycle in the preparation of raw material 2-methyl-4-amino-5-(methane amide methyl) pyrimidine of the present invention.Described concentrated after residuum be target product 2-methyl-4-amino-5-(amino methyl) pyrimidine.
In addition, according to method provided by the invention, the residuum after the method can also comprise described concentrating carries out dry step.The method of described drying can be the various methods that this area routine uses, such as constant pressure and dry, vacuum-drying etc.Under preferable case, described drying means adopts boulton process, and described vacuum drying vacuum tightness is 0.05-0.09MPa, and temperature is 50-80 DEG C, and the time is 3-5 hour.
Below will be described the present invention by embodiment.
In following examples,
The content of 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and 2-methyl-4-amino-5-(amino methyl) pyrimidine carried out mensuration by the high performance liquid chromatograph of the LC-20AT model using Shimadzu Corporation.
If not otherwise specified, used reagent is commercially available reagent.
Preparation example
2-methyl-4-amino-5-(methane amide methyl) pyrimidine used in the present invention is with reference to the method preparation in " synthesis of 2-methyl-4-amino-5-methane amide methylpyrimidine " (application chemical industry, the 34th volume the 8th phase in 2005).
Embodiment 1
2-methyl-4-amino-5-(methane amide methyl) pyrimidine, 720ml methyl alcohol and the 2g sodium methylate that 100g preparation example are obtained join in the autoclave of 1000ml, open and stir, insulation reaction 8h at 100 DEG C, then reaction gained mixture is cooled to 50 DEG C, suction filtration gained filtrate is also transferred in there-necked flask and is carried out air distillation and concentrate by suction filtration, obtain methyl-formiate 23ml, reclaim methyl alcohol 635ml.Be vacuum-drying 3 hours at 0.05MPa and temperature are 80 DEG C by the residuum after concentrated in vacuum tightness, obtain faint yellow solid 61.9g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 99.6%.
Embodiment 2
2-methyl-4-amino-5-(methane amide methyl) pyrimidine, 482ml methyl alcohol and the 1g sodium methylate that 100g preparation example are obtained join in the autoclave of 1000ml, open and stir, insulation reaction 2h at 120 DEG C, then reaction gained mixture is cooled to 25 DEG C, suction filtration gained filtrate is also transferred in there-necked flask and is carried out air distillation and concentrate by suction filtration, obtain methyl-formiate 21ml, reclaim methyl alcohol 392ml.Be vacuum-drying 5 hours at 0.09MPa and temperature are 50 DEG C by the residuum after concentrated in vacuum tightness, obtain faint yellow solid 58.2g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 99.2%.
Embodiment 3
2-methyl-4-amino-5-(methane amide methyl) pyrimidine, 970ml methyl alcohol and the 0.5g sodium methylate that 100g preparation example are obtained join in the autoclave of 1500ml, open and stir, insulation reaction 10h at 90 DEG C, then reaction gained mixture is cooled to 35 DEG C, suction filtration gained filtrate is also transferred in single port flask and is carried out underpressure distillation and concentrate by suction filtration, obtain methyl-formiate 20ml, reclaim methyl alcohol 879ml.Be vacuum-drying 4 hours at 0.08MPa and temperature are 60 DEG C by the residuum after concentrated in vacuum tightness, obtain faint yellow solid 57.6g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 99.3%.
Embodiment 4
2-methyl-4-amino-5-(amino methyl) pyrimidine is prepared according to the method for embodiment 1, unlike, adopt the triethylamine of identical amount to substitute sodium methylate, obtain faint yellow solid 26.2g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 98.9%.
Embodiment 5
2-methyl-4-amino-5-(amino methyl) pyrimidine is prepared according to the method for embodiment 1, unlike, the add-on of methyl alcohol is 220ml, obtains faint yellow solid 34.6g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 98.5%.
Embodiment 6
2-methyl-4-amino-5-(amino methyl) pyrimidine is prepared according to the method for embodiment 1, unlike, the add-on of sodium methylate is 0.2g, obtains faint yellow solid 38.9g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 99.3%.
Embodiment 7
2-methyl-4-amino-5-(amino methyl) pyrimidine is prepared according to the method for embodiment 1, unlike, the add-on of sodium methylate is 5.0g, obtains faint yellow solid 62.6g.Detecting 2-methyl-4-amino-5-(amino methyl) pyrimidine content through HPLC is 96.7%.
As can be seen from the above embodiments, preparation method according to 2-methyl-4-amino-5-(amino methyl) pyrimidine provided by the invention can not produce a large amount of organic salt, inorganic salt and waste liquid, and by product and residue methyl alcohol can all recyclings, the method economy, environmental protection, meet the demand for development of current national energy-conserving and environment-protective industrial economy.Meanwhile, the method is simple to operate, product is easy to separation and purification, is applicable to suitability for industrialized production.
More than describe the preferred embodiment of the present invention in detail; but the present invention is not limited to the detail in above-mentioned embodiment, within the scope of technical conceive of the present invention; can carry out multiple simple variant to technical scheme of the present invention, these simple variant all belong to protection scope of the present invention.
It should be noted that in addition, each concrete technical characteristic described in above-mentioned embodiment, in reconcilable situation, can be combined by any suitable mode, in order to avoid unnecessary repetition, the present invention illustrates no longer separately to various possible array mode.
In addition, also can carry out arbitrary combination between various different embodiment of the present invention, as long as it is without prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.

Claims (7)

1. the preparation method of 2-methyl-4-amino-5-(amino methyl) pyrimidine, it is characterized in that, the method comprises: under the existence of alkaline agent, 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol are carried out contact reacts, the weight ratio of the consumption of described alkaline agent and the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine is 0.001-0.05:1, and described alkaline agent is one or more in sodium methylate, sodium ethylate, ethamine, diethylamine, triethylamine, methylamine, dimethylamine and ammonia; The mol ratio of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and described methyl alcohol is 1:1-100.
2. preparation method according to claim 1, wherein, the mol ratio of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and described methyl alcohol is 1:20-40.
3. preparation method according to claim 1, wherein, the weight ratio of the consumption of described alkaline agent and the consumption of described 2-methyl-4-amino-5-(methane amide methyl) pyrimidine is 0.005-0.02:1.
4. preparation method according to claim 3, wherein, described alkaline agent is sodium methylate.
5. preparation method according to claim 1, wherein, described catalytic condition comprises: temperature of reaction is 60-150 DEG C, and the reaction times is 1-30 hour.
6. preparation method according to claim 5, wherein, described catalytic condition comprises: temperature of reaction is 90-120 DEG C, and the reaction times is 2-10 hour.
7. preparation method according to claim 1, wherein, the method step of carrying out solid-liquid separation and described solid-liquid separation gained filtrate is concentrated after also comprising the mixture cooling that 2-methyl-4-amino-5-(methane amide methyl) pyrimidine and methyl alcohol contact reacts are obtained.
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CN107602482A (en) * 2017-09-05 2018-01-19 常州大学 A kind of 2 methyl 4 amino 5 (formyl aminomethyl) pyrimidine hydrolysis process

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CN107602481A (en) * 2017-09-05 2018-01-19 常州大学 A kind of 2 methyl 4 amino 5 (formyl aminomethyl) pyrimidine hydrolysis process
CN109293580A (en) * 2018-12-04 2019-02-01 南京金浩医药科技有限公司 A kind of preparation process of 2- methyl -4- amino -5- aminomethyl pyrimidine

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