CN103755645A - Synthetic process of compound pyrrole alkyl amino pyrimidine oxide - Google Patents
Synthetic process of compound pyrrole alkyl amino pyrimidine oxide Download PDFInfo
- Publication number
- CN103755645A CN103755645A CN201310729195.9A CN201310729195A CN103755645A CN 103755645 A CN103755645 A CN 103755645A CN 201310729195 A CN201310729195 A CN 201310729195A CN 103755645 A CN103755645 A CN 103755645A
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- China
- Prior art keywords
- oxide compound
- pyrrolidyl
- amino
- compound
- pyrimidine oxide
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- TZAQCXLKWKDFQB-UHFFFAOYSA-N NC(C1)=NC(N2CCCC2)=CC(N=[IH])=C1O Chemical compound NC(C1)=NC(N2CCCC2)=CC(N=[IH])=C1O TZAQCXLKWKDFQB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
Abstract
The invention provides a synthetic process of a compound pyrrole alkyl amino pyrimidine oxide. The process comprises the following steps: (1) oxidizing reaction; and (2) substitution reaction. According to the synthetic process, 2,4-diamino-6-cloro pyridine is taken as a raw material, and the pyrrole alkyl amino pyrimidine oxide is obtained by oxidization and substitution. The synthetic process has the advantages of being low in cost, simple in reaction step, low in toxicity, convenient in technological operation, high in yield, and applicable to industrial production.
Description
Technical field
The synthesis technique that the present invention relates to a kind of compound pyrrolidyl di-amino-pyrimidine oxide compound, belongs to technical field of chemical synthesis.
Background technology
Chemistry 6-by name pyrrolidyl-2 of pyrrolidyl di-amino-pyrimidine oxide compound, 4-di-amino-pyrimidine-3-oxide compound (6-(pyrrolidin-1-yl) pyrimidine-2,4-diamine-3-oxide), its structural formula is:
Pyrrolidyl di-amino-pyrimidine oxide compound is a kind of novel hair growth promoter compound, its can promote telogen in hair life cycle to anagen change, and maintain for a long time make anagen, thereby promote the growth of hair; In addition, it also can be used as the raw material of the anti-product-stripping mechanism of hair.
Yet the synthesis technique report about pyrrolidyl di-amino-pyrimidine oxide compound does not almost have both at home and abroad.
Summary of the invention
The object of this invention is to provide a kind of synthetic route simple, production cost is low, the synthesis technique of the pyrrolidyl di-amino-pyrimidine oxide compound of the applicable suitability for industrialized production that productive rate is high.
Technical scheme of the present invention is: adopting 2,4-diamino-6-chloropyrimide is raw material, through oxidation, replaces and obtains pyrrolidyl di-amino-pyrimidine oxide compound.Concrete synthesis step is as follows:
1) oxidizing reaction: with dissolution with solvents raw material 2,4-diamino-6-chloropyrimide, add superoxide to gradation in the raw mixture obtaining, react under room temperature, filter, obtain 2,4-diamino-6-chloropyrimide oxide compound;
2) substitution reaction: water dissolving step 1 products therefrom, in the mixture obtaining, add tetramethyleneimine, after stirring, add alkali, heating is reacted, the reaction solution cooled and filtered obtaining, washes filter cake be dried, and obtains product pyrrolidyl di-amino-pyrimidine oxide compound.
In above synthesis step, the solvent in described step 1 is one or more the mixture in methyl alcohol, ethanol, Virahol; Described superoxide is a kind of in hydrogen peroxide, Peracetic Acid, metachloroperbenzoic acid; Described 2, the mass ratio of 4-diamino-6-chloropyrimide, solvent, superoxide is 1:8～12:2～4, and the reaction times is 12～36 hours.
Alkali in described step 2 is one or more the mixture in sodium hydroxide, potassium hydroxide, triethylamine; Described 2, the mol ratio of 4-diamino-6-chloropyrimide oxide compound, tetramethyleneimine, alkali is 1:1～2:1～2, and temperature of reaction is 60～90 ℃, and the reaction times is 1～3 hour.
Synthetic route is as follows:
Superoxide in step 1 of the present invention adds in batches, to guarantee its metastable concentration, is beneficial to the carrying out of oxidizing reaction, and in step 2, directly water is cooked solvent; After two-step reaction finishes, be all that direct filtration obtains product, simple to operate, cost-saving again, be applicable to very much suitability for industrialized production.
The beneficial effect that the present invention produces is: synthesis technique provided by the invention has the advantages such as operation is simple, easy and simple to handle, product postprocessing is simple, yield is high, production cost is low; The product purity that obtains is high, steady quality, and the raw material that reacts required is easy to get, cheap, is applicable to very much large-scale industrial production.
Embodiment
Below in conjunction with embodiment, the invention will be further described.
Embodiment 1
Concrete synthesis step of the present invention is as follows:
(1) oxidizing reaction:
Get 100 gram 2,4-diamino-6-chloropyrimide and 800 grams of ethanol are inserted in there-necked flask and are mixed, and under stirring, with ice-water bath, are cooled to below 5 ℃, drip 120 grams of Peracetic Acid at this temperature, react 6 hours under room temperature; Reaction solution is cooled to below 5 ℃ again, drip the Peracetic Acid of 120 grams, then at room temperature reaction is spent the night again, and be again cooled to reaction solution below 5 ℃ next day, continue to drip 60 grams of Peracetic Acid, then at room temperature react after 6 hours, finish reaction, filter, dry, obtain 100 gram 2,4-diamino-6-chloropyrimide oxide solid, this step yield is 90%.
(2) substitution reaction:
Get 100 gram 2,4-diamino-6-chloropyrimide oxide compound and 300 grams of water are inserted in there-necked flask and are mixed, add while stirring 50 grams of tetramethyleneimine and 30 grams of sodium hydroxide, be heated to 80 ℃ of reactions 2 hours, reaction finishes, and is cooled to room temperature, filter, dry after filter cake washing, obtain 103 grams of pyrrolidyl di-amino-pyrimidine oxide solids, this step yield is 85%.
The yield of whole synthesis technique is 76.5% above.
Claims (6)
1. a synthesis technique for compound pyrrolidyl di-amino-pyrimidine oxide compound, is characterized in that, described technique comprises the following steps:
1) oxidizing reaction: with dissolution with solvents raw material 2,4-diamino-6-chloropyrimide, add superoxide to gradation in the raw mixture obtaining, react after certain hour under room temperature, filter, obtain 2,4-diamino-6-chloropyrimide oxide compound;
2) substitution reaction: water dissolving step 1 products therefrom, in the mixture obtaining, add appropriate tetramethyleneimine, after stirring, add alkali, heating is reacted, the reaction solution cooled and filtered obtaining, washes filter cake be dried, and can obtain product pyrrolidyl di-amino-pyrimidine oxide compound.
2. the synthesis technique of a kind of compound pyrrolidyl di-amino-pyrimidine oxide compound according to claim 1, is characterized in that solvent in described step 1 is one or more the mixture in methyl alcohol, ethanol, Virahol.
3. the synthesis technique of a kind of compound pyrrolidyl di-amino-pyrimidine oxide compound according to claim 1, is characterized in that superoxide in described step 1 is a kind of in hydrogen peroxide, Peracetic Acid, metachloroperbenzoic acid.
4. the synthesis technique of a kind of compound pyrrolidyl di-amino-pyrimidine oxide compound according to claim 1, it is characterized in that described step 1 Raw 2, the mass ratio of 4-diamino-6-chloropyrimide, solvent, superoxide is 1:8～12:2～4, and the reaction times is 12～36 hours.
5. the synthesis technique of a kind of compound pyrrolidyl di-amino-pyrimidine oxide compound according to claim 1, is characterized in that alkali in described step 2 is one or more the mixture in sodium hydroxide, potassium hydroxide, triethylamine.
6. the synthesis technique of a kind of compound pyrrolidyl di-amino-pyrimidine oxide compound according to claim 1, it is characterized in that in described step 22, the mol ratio of 4-diamino-6-chloropyrimide oxide compound, tetramethyleneimine, alkali is 1:1～2:1～2, temperature of reaction is 60～90 ℃, and the reaction times is 1～3 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310729195.9A CN103755645A (en) | 2013-12-26 | 2013-12-26 | Synthetic process of compound pyrrole alkyl amino pyrimidine oxide |
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| CN201310729195.9A CN103755645A (en) | 2013-12-26 | 2013-12-26 | Synthetic process of compound pyrrole alkyl amino pyrimidine oxide |
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| CN103755645A true CN103755645A (en) | 2014-04-30 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107235919A (en) * | 2017-06-22 | 2017-10-10 | 安徽拜善晟制药有限公司 | A kind of synthesis technique of minoxidil |
| CN107550749A (en) * | 2017-10-15 | 2018-01-09 | 广州汀兰生物科技有限公司 | A kind of hair growth composition and its application |
| CN108210937A (en) * | 2018-02-08 | 2018-06-29 | 上海应用技术大学 | Pyrrole alkyl amino pyrimidine oxide beta-cyclodextrin base inclusion compound and preparation method thereof |
| CN111018838A (en) * | 2019-11-25 | 2020-04-17 | 重庆东寰科技开发有限公司 | Synthesis method of pyrrolidinyl diaminopyrimidine oxynitride |
| CN114773275A (en) * | 2022-05-30 | 2022-07-22 | 国药集团化学试剂有限公司 | Preparation method of 2, 4-diamino-6-chloropyrimidine oxynitride |
-
2013
- 2013-12-26 CN CN201310729195.9A patent/CN103755645A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107235919A (en) * | 2017-06-22 | 2017-10-10 | 安徽拜善晟制药有限公司 | A kind of synthesis technique of minoxidil |
| CN107235919B (en) * | 2017-06-22 | 2020-05-12 | 安徽拜善晟制药有限公司 | Process for synthesizing minoxidil |
| CN107550749A (en) * | 2017-10-15 | 2018-01-09 | 广州汀兰生物科技有限公司 | A kind of hair growth composition and its application |
| CN108210937A (en) * | 2018-02-08 | 2018-06-29 | 上海应用技术大学 | Pyrrole alkyl amino pyrimidine oxide beta-cyclodextrin base inclusion compound and preparation method thereof |
| CN111018838A (en) * | 2019-11-25 | 2020-04-17 | 重庆东寰科技开发有限公司 | Synthesis method of pyrrolidinyl diaminopyrimidine oxynitride |
| CN111018838B (en) * | 2019-11-25 | 2022-12-27 | 重庆东寰科技开发有限公司 | Synthesis method of pyrrolidinyl diaminopyrimidine oxynitride |
| CN114773275A (en) * | 2022-05-30 | 2022-07-22 | 国药集团化学试剂有限公司 | Preparation method of 2, 4-diamino-6-chloropyrimidine oxynitride |
| CN114773275B (en) * | 2022-05-30 | 2023-10-03 | 国药集团化学试剂有限公司 | Preparation method of 2, 4-diamino-6-chloropyrimidine nitrogen oxide |
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Application publication date: 20140430 |