Unlock instant, AI-driven research and patent intelligence for your innovation.
A kind of method for preparing pyrimidine compound from methyl ketone compound and nitrile compound
What is Al technical title?
Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
A technology of compounds and pyrimidines, which is applied in the field of preparation of pyrimidines, can solve the problems of harsh reaction conditions and limited product applicability, and achieve the effects of simple reaction operation, easy separation, and wide applicability
Active Publication Date: 2021-08-31
HUNAN UNIV
View PDF1 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
Recently, Xie et al. reported the synthesis of pyrimidines by intermolecular cycloaddition of nitriles and prefunctionalized alkynes under TfOH conditions (Nat. Commun. 2016, 7, 10914-10922), but these reactions are mostly Multi-step reaction, the applicability of the product is not wide, the use of precious metals or substrates requires pre-functionalization, and the reaction conditions are harsh
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
Synthetic example 1
[0022] Synthesis of 2,4-Dimethyl-6-phenylpyrimidine
[0025] Synthesis of (4-fluorophenyl)-2,6-dimethylpyrimidine
[0026] Add 0.30mmol 4-fluoroacetophenone, 0.06mmol copper bromide, 0.60mmol sodiumhydroxide, and 0.6mL acetonitrilesolvent into the reactor. Under a nitrogen atmosphere, heat to 110°C, continue stirring for 24 hours, stop the reaction, cool to room temperature, add saturated ammoniumchloride solution for washing, extract with dichloromethane, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography. The target product was obtained with a yield of 85%. 1 H NMR (400MHz, CDCl 3 ):δ8.05(dd,J=8.4,5.2Hz,2H),7.32(s,1H),7.16(t,J=8.6Hz,2H),2.74(s,3H),2.54(s,3H) .
Synthetic example 3
[0028] Synthesis of (4-chlorophenyl)-2,6-dimethylpyrimidine
[0029] Add 0.30mmol 4-chloroacetophenone, 0.03mmol copper chloride, 0.60mmol sodiumhydroxide, and 0.6mL acetonitrile solvent into the reactor. Under a nitrogen atmosphere, heat to 110°C, continue stirring for 24 hours, stop the reaction, cool to room temperature, add saturated ammonium chloride solution for washing, extract with dichloromethane, dry, and distill off the solvent under reduced pressure. The crude product is separated by column chromatography. The target product was obtained with a yield of 82%. 1 H NMR (400MHz, CDCl 3 ): δ7.97(d, J=8.5Hz, 2H), 7.42(d, J=8.5Hz, 2H), 7.28(d, J=15.6Hz, 1H), 2.72(s, 3H), 2.52(s ,3H).
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
PUM
Login to View More
Abstract
The invention provides a method for synthesizing pyrimidine compounds from methyl ketone compounds and nitrile compounds. The method is carried out under a nitrogenatmosphere, uses a copper catalyst and an alkali reagent, and directly uses methyl ketone compounds and nitrile compounds as raw materials to synthesize pyrimidine compounds. The method uses cheap and easy-to-obtain raw materials and copper catalysts, does not use special reaction conditions such as ligands, acids, peroxides, and microwaveradiation. The substrate does not need to be pre-functionalized and has a wide range of applicability. The reaction conditions are mild and the operation is simple. The product yields are high, and have potential application prospects in pesticides and bioactive drugs.
Description
【Technical field】 [0001] The invention relates to the fields of organic synthesis and pesticidemedicine, in particular to a method for preparing pyrimidine compounds from methyl ketone compounds and nitrile compounds. 【Background technique】 [0002] Pyrimidine is a very important six-membered nitrogen-containing heterocyclic compound. Many natural products contain pyrimidine structural units, and its derivatives have various biological activities such as insecticidal, bactericidal, herbicidal, antimalarial, and antiviral (Bioorg. Med.Chem.2005, 13, 6663–6671; J.Org.Chem.2016, 81, 11994–12000; Farmaco, 2003, 58, 1263–1270; Bioorg.Med.Chem.2005, 13, 4645–4650; ). Pyrimidine skeletons are widely present in many drug molecules, for example, vitamin B1, estrogen antagonists, antimalarials, anticoagulants, antineuropathic drugs, etc. Pyrimidine compounds not only have excellent biological activity but also have variable chemical structures. They are one of the hotspots in the r...
Claims
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.
Login to View More 
Login to View More