CN106883233A - The synthetic method of adenine and its derivative - Google Patents
The synthetic method of adenine and its derivative Download PDFInfo
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- CN106883233A CN106883233A CN201710108136.8A CN201710108136A CN106883233A CN 106883233 A CN106883233 A CN 106883233A CN 201710108136 A CN201710108136 A CN 201710108136A CN 106883233 A CN106883233 A CN 106883233A
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- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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Abstract
The invention discloses a kind of adenine and its synthetic method of derivative, it is first to obtain 2 tartronic acid diethylesters by the oxidized reaction of diethyl malonate and dimethyl dioxirane；Then 2 hydroxyl malonamides are obtained through ammonolysis reaction with ammoniacal liquor；Then 5 hydroxy pyrimidines 4,6 are obtained through ring-closure reaction with trimethyl orthoformate（1H,5H）Diketone；Again 4,5,6 trichloropyrimidines are obtained with phosgene through chlorination reaction；Again 4 chlorine 1H pyrazoles [3,4 d] pyrimidines are obtained with amitraz hydrochloride through ring-closure reaction；Finally adenine or derivatives thereof is obtained with ammoniacal liquor or aminated compounds through aminating reaction in the presence of triethyl amine.Synthetic method raw material of the invention is cheap and easy to get, and reaction condition is gentle, course of reaction safety, low to production equipment requirement, and especially environmental pollution is smaller, and yield is higher, so as to be adapted to industrialized production.
Description
Technical field
The present invention relates to medicine bioengineering chemical field, and in particular to the synthetic method of a kind of adenine and its derivative.
Background technology
Adenine, chemical name is adenine, is the constituent of nucleic acid, is mainly used in participating in organism
RNA and DNA synthesizes, and when leucocyte lacks, can promote leucocyte hyperplasia.There is adenine phytokinin to act on, its tablet
Or injection can be used for graininess leukopenia etc., it can also be used to prepare the medicine such as biochemical reagents and purine analog derivative, also
Can be used for blood storage.
At present, the synthetic method of adenine mainly has three kinds of adenosine method, hypoxanthine method and diethyl malonate method.
The deficiency of adenosine method is：Adenosine price is higher and limited source, causes production cost higher, so as to be not suitable for work
The big production of industryization.
Hypoxanthic deficiency is：Hypoxanthine is obtained by inosine cracking, therefore, the same price is higher and source has
Limit, same production cost is higher and be not suitable for industrialized production.
Diethyl malonate method has the advantages that raw material is cheap and easy to get relative to adenosine method and hypoxanthine method.But, it is existing
The synthetic route of some diethyl malonate methods is first to obtain 4,6- dihydroxy-pyrimidines through amitraz hydrochloride cyclization；Again through nitrification and
Chlorination obtains the chloro- 5- nitro-pyrimidines of 4,6- bis-；Then by the chloro- 5- nitro-pyrimidines of 4,6- bis- through ammoniacal liquor ammonification, sodium hydrosulfite reduction with
And formic acid cyclization obtain/or obtain adenine through iron powder reducing, formamide cyclization and ammoniacal liquor ammonification.
The deficiency of the method is：Yield is extremely low, and two kinds of adenine are especially prepared by the chloro- 5- nitro-pyrimidines of 4,6- bis-
Method yield can produce a large amount of waste liquids less than 50% using POCl3 chlorination and nitrification, cause environmental pollution
It is larger, so as to be also not suitable for industrialized production.
The content of the invention
It is an object of the invention to solve the above problems, there is provided a kind of production cost is relatively low, environmental pollution is smaller, yield
The synthetic method of adenine that is higher, being adapted to industrialized production and its derivative.
Realizing the technical scheme of above-mentioned purpose of the present invention is：A kind of synthetic method of adenine and its derivative, with
Lower step：
1. 2- tartronic acid diethylesters are obtained by the oxidized reaction of diethyl malonate and dimethyl dioxirane；
2. 2- hydroxyl malonamides are obtained through ammonolysis reaction by 2- tartronic acids diethylester and ammoniacal liquor；
3. 5- hydroxy pyrimidines -4,6- is obtained through ring-closure reaction by 2- hydroxyls malonamide and trimethyl orthoformate（1H,5H）- two
Ketone；
4. by 5- hydroxy pyrimidines -4,6-（1H,5H）- diketone obtains 4,5,6- trichloropyrimidines with phosgene through chlorination reaction；
5. chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- are obtained through ring-closure reaction by 4,5,6- trichloropyrimidines and amitraz hydrochloride；
6. by chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- and ammoniacal liquor or aminated compounds in the presence of triethyl amine through aminating reaction
Obtain adenine or derivatives thereof.
Above-mentioned steps oxidation reaction 1. is carried out in the presence of a catalyst；The catalyst is acetate, preferably
It is nickel acetate；The consumption of the catalyst is the 0.1%~1% of diethyl malonate weight.
Above-mentioned steps oxidation reaction 1. is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, second
Alcohol, isopropanol or n-butanol, preferably ethanol.
Above-mentioned steps 1. described in the mol ratio of diethyl malonate and the dimethyl dioxirane be 1: 1~1:
3, preferably 1: 1.5.
Above-mentioned steps oxidizing reaction temperature 1. is back flow reaction temperature.
Above-mentioned steps oxidation time 1. is 2~10h, preferably 5h.
Above-mentioned steps 2. described in the mol ratio of 2- tartronic acids diethylester and the ammoniacal liquor be 1: 1~1: 3, preferably
1∶2。
Above-mentioned steps ammonolysis reaction temperature 2. is 50~150 DEG C, preferably 90 DEG C；The ammonolysis reaction time is 1~5h, excellent
Elect 3h as.
Above-mentioned steps 3. described in the mol ratio of 2- hydroxyls malonamide and the trimethyl orthoformate be 1: 1~1: 3, it is excellent
Elect 1: 1 as.
Above-mentioned steps ring-closure reaction 3. is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, second
Alcohol, isopropanol or n-butanol, preferably ethanol.
Above-mentioned steps ring-closure reaction temperature 3. is room temperature（15~25 DEG C, similarly hereinafter）；Reaction time is 12h.
Above-mentioned steps 4. in be passed through phosgene temperature be -5~10 DEG C, preferably 0 DEG C；The time for being passed through phosgene is 1~3h.
Above-mentioned steps chlorination reaction 4. is carried out in the presence of NaOH.
Above-mentioned steps chlorination reaction 4. is carried out in dichloroethane solvent.
Above-mentioned steps 5. described in the mol ratio of 4,5,6- trichloropyrimidines and the amitraz hydrochloride be 1: 1~1: 3, preferably
It is 1: 1.
Above-mentioned steps ring-closure reaction 5. is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, second
Alcohol, isopropanol or n-butanol, preferably ethanol.
Above-mentioned steps ring-closure reaction temperature 5. is room temperature；Reaction time is 12h.
Above-mentioned steps 6. described in chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- and the ammoniacal liquor or aminated compounds mole
Than being 1: 1~1: 3, preferably 1: 1.1.
Above-mentioned steps 6. described in the mol ratio of chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- and the triethylamine be 1: 1~1:
3, preferably 1: 1.2.
Above-mentioned steps aminating reaction 6. is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, second
Alcohol, isopropanol or n-butanol, preferably ethanol.
Above-mentioned steps aminating reaction temperature 6. is back flow reaction temperature.
The above-mentioned steps aminating reaction time 6. is 2~10h, preferably 5h.
The good effect that the present invention has：Synthetic method raw material of the invention is cheap and easy to get, and reaction condition is gentle, reacts
Cheng Anquan, low to production equipment requirement, especially environmental pollution is smaller, and yield is higher, so as to be adapted to industrialized production.
Specific embodiment
（Embodiment 1）
The present embodiment is the synthetic method of adenine, and the route of the synthetic method is as follows：
。
The synthetic method has steps of：
1. by the diethyl malonate of 160g（1mol）It is dissolved in 300mL ethanol, adds the dimethyl dioxirane of 111g
（1.5mol）With the nickel acetate of 0.5g, backflow is then heated to, reacts 5h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 170g
2- tartronic acid diethylesters, yield is 96.6%.
2. by the 2- tartronic acid diethylesters of 176g（1mol）It is the ammoniacal liquor of 28wt% with 250g, concentration（2mol）Mixing,
90 DEG C are then heated to, 3h is reacted.
After reaction terminates, water is added, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain the 2- hydroxyls third of 115g
Diamides, yield is 97.5%.
3. at 0 DEG C, by the trimethyl orthoformate of 106g（1mol）It is dissolved in 200mL ethanol, is slowly added dropwise 100mL containing 118g
2- hydroxyl malonamides（1mol）Ethanol solution, drip off and be heated to 15~25 DEG C, stirring reaction 12h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 120g
5- hydroxy pyrimidines -4,6-（1H,5H）- diketone, yield is 93.8%.
4. by the 5- hydroxy pyrimidines -4,6- of 128g（1H,5H）- diketone（1mol）It is dissolved in 200mL dichloroethanes, at 0 DEG C,
Phosgene 2h is slowly introducing, has been led to（About 2h）15~25 DEG C are heated to, first stirring reaction 12h adds 100g, concentration for 30wt%
Sodium hydroxide solution, continue stirring reaction 3h.
After reaction terminates, water is added, extracted 3 times with dichloroethanes, organic layer is spin-dried for, obtain the 4 of 175g, 5,6- trichlorines
Pyrimidine, yield is 95.4%.
5. at 0 DEG C, by the amitraz hydrochloride of 80.5g（1mol）It is dissolved in 200mL ethanol, is slowly added dropwise 100mL and contains
The 4,5,6- trichloropyrimidines of 183.5g（1mol）Ethanol solution, drip off and be heated to 15~25 DEG C, stirring reaction 12h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 150g
Chloro- 1H- pyrazoles [3, the 4-d] pyrimidines of 4-, yield is 97.1%.
6. by chloro- 1H- pyrazoles [3,4-d] pyrimidines of the 4- of 154.5g（1mol）It is dissolved in 200mL ethanol, first adds 122g's
Triethylamine（1.2mol）, then it is slowly added dropwise the ammoniacal liquor that 138g, concentration are 28wt%（1.1mol）, drip off and be heated to backflow, reaction
5h。
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 130g
White solid adenine, yield is 96.3%.
（Embodiment 2）
The present embodiment is 6-Furfurylaminopurine（Namely kinetin）Synthetic method, the step of the method and embodiment 1 1.~5.
It is identical, difference be step 6.：By chloro- 1H- pyrazoles [3,4-d] pyrimidines of the 4- of 154.5g（1mol）It is dissolved in 200mL ethanol
In, first add the triethylamine of 122g（1.2mol）, then it is slowly added dropwise the 2- furylamines of 107g（1.1mol）, drip off heating
To flowing back, 5h is reacted.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 208g
White solid 6-Furfurylaminopurine, yield is 96.7%.
（Embodiment 3）
The present embodiment is oxyenadenine（Namely zeatin）Synthetic method, 1.~5. phase the step of the method is with embodiment 1
Together, difference be step 6.：By chloro- 1H- pyrazoles [3,4-d] pyrimidines of the 4- of 154.5g（1mol）It is dissolved in 200mL ethanol,
First add the triethylamine of 122g（1.2mol）, then it is slowly added dropwise the 4- amino-2-methyl -2- butenols of 111g（1.1mol）,
Drip off and be heated to backflow, react 5h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 212g
Pale powder oxyenadenine, yield is 96.8%.
（Embodiment 4）
The present embodiment is the synthetic method of carbonyl enadenine, the step of the method is with embodiment 1 1.~it is 5. identical, difference exists
In step 6.：By chloro- 1H- pyrazoles [3,4-d] pyrimidines of the 4- of 154.5g（1mol）It is dissolved in 200mL ethanol, first adds 122g's
Triethylamine（1.2mol）, then it is slowly added dropwise the 3- methyl-2-butene acid amides of 103g（1.1mol）, drip off and be heated to backflow, instead
Answer 5h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 210g
White powder carbonyl enadenine, yield is 96.8%.
（Embodiment 5）
The present embodiment is the synthetic method of isopentenyl gland purine, the step of the method is with embodiment 1 1.~it is 5. identical, difference
Place be step 6.：By chloro- 1H- pyrazoles [3,4-d] pyrimidines of the 4- of 154.5g（1mol）It is dissolved in 200mL ethanol, first adds
The triethylamine of 122g（1.2mol）, then it is slowly added dropwise the 4- amino-2-methyl -2- butylene of 93g（1.1mol）, drip off and be heated to
Backflow, reacts 5h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 196g
White powder isopentenyl gland purine, yield is 96.6%.
（Embodiment 6）
The present embodiment is the synthetic method of 6-benzyl aminopurine, 1.~5. identical, difference the step of the method is with embodiment 1
Be step 6.：By chloro- 1H- pyrazoles [3,4-d] pyrimidines of the 4- of 154.5g（1mol）It is dissolved in 200mL ethanol, first adds 122g
Triethylamine（1.2mol）, then it is slowly added dropwise the benzylamine of 118g（1.1mol）, drip off and be heated to backflow, react 5h.
After reaction terminates, ethanol is evaporated, adds water, be extracted with ethyl acetate 3 times, organic layer is spin-dried for, obtain 216g
White needles 6-benzyl aminopurine, yield is 96.0%.
Table 1
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 | |
| Target compound | Adenine | 6-Furfurylaminopurine | Oxyenadenine | Carbonyl enadenine | Isopentenyl gland purine | 6-benzyl aminopurine |
| Ammoniacal liquor/aminated compounds | 138g, concentration are the ammoniacal liquor of 28wt% | The 2- furylamines of 107g | 4- amino-2-methyls-the 2- of 111g Butenol | The 3- methyl-2-butene acyls of 103g Amine | 4- amino-2-methyls-the 2- of 93g Butylene | The benzylamine of 118g |
| Target product | The adenine of 130g | The 6-Furfurylaminopurine of 208g | The oxyenadenine of 212g | The carbonyl enadenine of 210g | The isopentenyl gland purine of 196g | The 6-benzyl aminopurine of 216g |
| Yield | 96.3% | 96.7% | 96.8% | 96.8% | 96.6% | 96.0% |
Claims (9)
1. the synthetic method of a kind of adenine and its derivative, it is characterised in that have steps of：
1. 2- tartronic acid diethylesters are obtained by the oxidized reaction of diethyl malonate and dimethyl dioxirane；
2. 2- hydroxyl malonamides are obtained through ammonolysis reaction by 2- tartronic acids diethylester and ammoniacal liquor；
3. 5- hydroxy pyrimidines -4,6- is obtained through ring-closure reaction by 2- hydroxyls malonamide and trimethyl orthoformate（1H,5H）- two
Ketone；
4. by 5- hydroxy pyrimidines -4,6-（1H,5H）- diketone obtains 4,5,6- trichloropyrimidines with phosgene through chlorination reaction；
5. chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- are obtained through ring-closure reaction by 4,5,6- trichloropyrimidines and amitraz hydrochloride；
6. by chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- and ammoniacal liquor or aminated compounds in the presence of triethyl amine through aminating reaction
Obtain adenine or derivatives thereof.
2. the synthetic method of adenine according to claim 1 and its derivative, it is characterised in that：Above-mentioned steps oxygen 1.
Change reaction is carried out in the presence of a catalyst；The catalyst is preferably nickel acetate；The consumption of the catalyst is the third two
The 0.1%~1% of diethyl phthalate weight.
3. the synthetic method of adenine according to claim 1 and its derivative, it is characterised in that：Above-mentioned steps 1. middle institute
It is 1: 1~1: 3, preferably 1: 1.5 that diethyl malonate is stated with the mol ratio of the dimethyl dioxirane.
4. the synthetic method of adenine according to claim 1 and its derivative, it is characterised in that：Above-mentioned steps oxygen 1.
Change reaction is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, ethanol, isopropanol or n-butanol；On
Step oxidizing reaction temperature 1. is stated for back flow reaction temperature；Above-mentioned steps oxidation time 1. is 2~10h.
5. according to the described adenine of one of Claims 1-4 and its synthetic method of derivative, it is characterised in that：Above-mentioned step
It is rapid 2. described in the mol ratio of 2- tartronic acids diethylester and the ammoniacal liquor be 1: 1~1: 3, preferably 1: 2；Above-mentioned steps are 2.
Ammonolysis reaction temperature be 50~150 DEG C, the ammonolysis reaction time be 1~5h.
6. according to the described adenine of one of Claims 1-4 and its synthetic method of derivative, it is characterised in that：Above-mentioned step
It is rapid 3. described in the mol ratio of 2- hydroxyls malonamide and the trimethyl orthoformate be 1: 1~1: 3；Above-mentioned steps cyclization 3.
Reaction is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, ethanol, isopropanol or n-butanol.
7. according to the described adenine of one of Claims 1-4 and its synthetic method of derivative, it is characterised in that：Above-mentioned step
It is rapid 4. in be passed through the temperature of phosgene be -5~10 DEG C, the time for being passed through phosgene is 1~3h；Above-mentioned steps chlorination reaction 4. be
Carried out in the presence of NaOH；Above-mentioned steps chlorination reaction 4. is carried out in dichloroethane solvent.
8. according to the described adenine of one of Claims 1-4 and its synthetic method of derivative, it is characterised in that：Above-mentioned step
It is rapid 5. described in the mol ratio of 4,5,6- trichloropyrimidines and the amitraz hydrochloride be 1: 1~1: 3, preferably 1: 1；Above-mentioned steps
5. ring-closure reaction is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, ethanol, isopropanol or positive fourth
Alcohol.
9. according to the described adenine of one of Claims 1-4 and its synthetic method of derivative, it is characterised in that：Above-mentioned step
It is rapid 6. described in the mol ratio of chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- and the ammoniacal liquor or aminated compounds be 1: 1~1: 3；
Above-mentioned steps 6. described in the mol ratio of chloro- 1H- pyrazoles [3,4-d] pyrimidines of 4- and the triethylamine be 1: 1~1: 3；Above-mentioned step
Rapid aminating reaction 6. is carried out in the presence of alcohols solvent；The alcohols solvent is methyl alcohol, ethanol, isopropanol or just
Butanol；Above-mentioned steps aminating reaction temperature 6. is back flow reaction temperature；The above-mentioned steps aminating reaction time 6. is 2~10h.
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| CN108864099A (en) * | 2018-09-08 | 2018-11-23 | 湖北荆洪生物科技股份有限公司 | A kind of synthetic method of high-purity 6-Furfurylaminopurine |
| CN110563582A (en) * | 2019-10-09 | 2019-12-13 | 合肥诚志生物制药有限公司 | Process for preparing 2-hydroxy-2-phenyl-malonamide |
| CN111560019A (en) * | 2020-05-11 | 2020-08-21 | 安徽京和生物药业科技有限公司 | Method for synthesizing isopentenyl adenine or derivatives thereof by one-step method |
| CN111662293A (en) * | 2020-06-23 | 2020-09-15 | 成都工业学院 | Preparation method of zeatin |
| CN116535407A (en) * | 2023-05-08 | 2023-08-04 | 河南省精细化工研究院有限公司 | Preparation process of plant endogenous cytokinin enadenine |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108864099A (en) * | 2018-09-08 | 2018-11-23 | 湖北荆洪生物科技股份有限公司 | A kind of synthetic method of high-purity 6-Furfurylaminopurine |
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| CN110563582A (en) * | 2019-10-09 | 2019-12-13 | 合肥诚志生物制药有限公司 | Process for preparing 2-hydroxy-2-phenyl-malonamide |
| CN111560019A (en) * | 2020-05-11 | 2020-08-21 | 安徽京和生物药业科技有限公司 | Method for synthesizing isopentenyl adenine or derivatives thereof by one-step method |
| CN111662293A (en) * | 2020-06-23 | 2020-09-15 | 成都工业学院 | Preparation method of zeatin |
| CN111662293B (en) * | 2020-06-23 | 2021-10-22 | 成都工业学院 | Preparation method of zeatin |
| CN116535407A (en) * | 2023-05-08 | 2023-08-04 | 河南省精细化工研究院有限公司 | Preparation process of plant endogenous cytokinin enadenine |
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