CN104447577A - Pyrimidine derivative and preparation method thereof - Google Patents
Pyrimidine derivative and preparation method thereof Download PDFInfo
- Publication number
- CN104447577A CN104447577A CN201410683112.1A CN201410683112A CN104447577A CN 104447577 A CN104447577 A CN 104447577A CN 201410683112 A CN201410683112 A CN 201410683112A CN 104447577 A CN104447577 A CN 104447577A
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- China
- Prior art keywords
- preparation
- methyl
- pyrimidine derivative
- pyrimidine derivatives
- compound
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- 0 CSc1ncc(C(O*)=O)c(*)n1 Chemical compound CSc1ncc(C(O*)=O)c(*)n1 0.000 description 2
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
- C07D239/56—One oxygen atom and one sulfur atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a pyrimidine derivative and a preparation method thereof. The pyrimidine derivative has the structural formula shown in the description, in the formula, R is selected from methyl, ethyl or isopropyl. Meanwhile, the invention provides a preparation method for the pyrimidine derivative. The preparation method for the pyrimidine derivative has the advantages as follows: the reaction condition is mild, no pollution is achieved, raw materials are easy to obtain, the total yield is high, and product purity is high.
Description
Technical field
The present invention relates to a kind of pyrimidine derivatives and preparation method thereof, belong to pharmaceutical intermediate synthesis field.
Background technology
Pyrimidine derivatives is extensively present in organism and occurring in nature, its structural performance and biological activity, at physiology, pharmacologically all plays an important role.As reacting precursor, be pharmacophore useful in pharmaceutical synthesis, a lot of drug molecule is all derived by pyrimidine compound.
Summary of the invention
The invention provides a kind of pyrimidine derivatives with following structural formula,
In formula, R is selected from methyl, ethyl or sec.-propyl.
The present invention provides a kind of preparation method of above-mentioned pyrimidine derivatives simultaneously, and synthetic route is:
In formula, R is selected from methyl, ethyl or sec.-propyl;
Comprise the following steps:
(1) raw material 1 obtains compound 2 through thiocarbamide methylation reaction;
(2) after the 2-in-1 ring of compound, acidifying generates compound 4.
Preferably, in described step (1), thiocarbamide methylating reagent is methyl-sulfate.
Preferably, in described step (2), cyclization reagent is
Preparation of pyrimidine derivatives provided by the invention at least has the following advantages: reaction conditions is gentle, and pollution-free, raw material is cheap and easy to get, and total recovery is high, and product purity is high.
Embodiment
Below will describe the present invention.But these embodiments do not limit the present invention, the conversion in the method that those of ordinary skill in the art makes according to these embodiments is all included in protection scope of the present invention.
In the compounds of this invention 3 ~ 4, R is selected from methyl, ethyl or sec.-propyl, and preparation method is below that methyl is introduced with R, it may occur to persons skilled in the art that the method is equally applicable to ethyl and sec.-propyl.
Embodiment 1: prepare compound 2
In there-necked flask, add 100g raw material 1 urea and 300ml water, drip 90g methyl-sulfate, drip and finish, be warming up to 70 DEG C ~ 80 DEG C, reaction 8h, cooling, suction filtration, dry 213g compound 2, yield 92.3%.
Embodiment 2: prepare compound 4
60g compound 2,35g methoxy methylene radical dimethyl malonate and 120ml ethanol is added in there-necked flask, dripping 120ml massfraction is the aqueous sodium hydroxide solution of 20%, drip and finish, 20 DEG C ~ 30 DEG C reaction 5h are salt acid for adjusting pH value to 2 ~ 3 of 20% with massfraction, suction filtration, solid drying, obtain 52g compound 4, yield 60.2%, purity 98.6%.HNMR(DMSO，300MHz)δ:13.2(br,1H),8.42(s,1H),3.72(s,3H),2.56(s,3H)。
Be to be understood that, although this specification sheets is described according to embodiment, but not each embodiment only comprises an independently technical scheme, this narrating mode of specification sheets is only for clarity sake, those skilled in the art should by specification sheets integrally, technical scheme in each embodiment also through appropriately combined, can form other embodiments that it will be appreciated by those skilled in the art that.
A series of detailed description listed is above only illustrating for feasibility embodiment of the present invention; they are also not used to limit the scope of the invention, all do not depart from the skill of the present invention equivalent implementations done of spirit or change all should be included within protection scope of the present invention.
Claims (4)
1. a pyrimidine derivatives, has following structural formula:
In formula, R is selected from methyl, ethyl or sec.-propyl.
2. a preparation method for pyrimidine derivatives described in claim 1, is characterized in that, synthetic route is:
In formula, R is selected from methyl, ethyl or sec.-propyl;
Comprise the following steps:
(1) raw material 1 obtains compound 2 through thiocarbamide methylation reaction;
(2) after the 2-in-1 ring of compound, acidifying generates compound 4.
3. the preparation method of pyrimidine derivatives according to claim 2, is characterized in that, in described step (1), thiocarbamide methylating reagent is methyl-sulfate.
4. the preparation method of pyrimidine derivatives according to claim 2, is characterized in that, in described step (2), cyclization reagent is
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410683112.1A CN104447577A (en) | 2014-11-24 | 2014-11-24 | Pyrimidine derivative and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410683112.1A CN104447577A (en) | 2014-11-24 | 2014-11-24 | Pyrimidine derivative and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104447577A true CN104447577A (en) | 2015-03-25 |
Family
ID=52894406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410683112.1A Pending CN104447577A (en) | 2014-11-24 | 2014-11-24 | Pyrimidine derivative and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104447577A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013163159A2 (en) * | 2012-04-24 | 2013-10-31 | Board Of Trustees Of Northern Illinois University | Design and synthesis of novel inhibitors of isoprenoid biosynthesis |
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2014
- 2014-11-24 CN CN201410683112.1A patent/CN104447577A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013163159A2 (en) * | 2012-04-24 | 2013-10-31 | Board Of Trustees Of Northern Illinois University | Design and synthesis of novel inhibitors of isoprenoid biosynthesis |
Non-Patent Citations (3)
| Title |
|---|
| STEPHANIE FEDERICO,ET AL.: "Scaffold Decoration at Positions 5 and 8 of 1,2,4-Triazolo[1,5-c]Pyrimidines to Explore the Antagonist Profiling on Adenosine Receptors: A Preliminary Structure-Activity Relationship Study", 《JOURNAL OF MEDICINAL CHEMISTRY》 * |
| 奚绍祁,等: "吡哌酸（Pipemidic Acid）的合成", 《沈阳药学院学报》 * |
| 张彦，许响生.: "2-甲硫基-4-羟基-5-嘧啶甲酸甲酯的合成", 《化工生产与技术》 * |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20150325 |