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2-amido pyrimidine compound and preparation method thereof

A technology for aminopyrimidines and compounds, applied in the field of 2-aminopyrimidine compounds and their preparation, can solve the problems of low efficiency, many reaction steps, harsh reaction conditions, etc., and achieve cost reduction, good specificity, and reaction system simple effect

Inactive Publication Date: 2015-06-24
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(a) Wendelin, W.; Schermanz, K.; Schweiger, K.; Fuchsgruber, A. Monatsh. Chem. 1983, 114, 1371. (b) Erian, A.W. ) Lagoja, I.M.Chem. Biodiversity, 2005, 2, 1. (d) Bagley, M.C.; Hughes, D.D.; Taylor, P.H. Synlett, 2003, 259. (e) Karpov, A.S.; , 5, 3451. (f) Karpov, A.S.; Müller, T.J.J.Synthesis, 2003, 2815. (g) D'Souza, D.M.; Müller, T.J.J.Nat.Protoc., 2008, 3, 1660. (h) Santra, S Dhara, K.; Ranjan, P.; Bera, P.; Dash, J.; Mandal, S.K. Green Chem., 2011, 13, 3238. (i) Chauhan, S.M.S.; 1779. (j) Marzinzik, A.L.; Felder, E.R.J.Org.Chem. 1998, 63, 724. (k) Zhu, S.; Shi, S.; Gerritz, S.W.; ) Bannwarth, P.; Valleix, A.; Grée, D.; Grée, R.J.Org.Chem.2009, 74, 4646. However, these methods usually have the disadvantages of many reaction steps, low efficiency, harsh reaction conditions, etc., so the development An efficient and green method for the synthesis of 2-aminopyrimidine derivatives is of great interest

Method used

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  • 2-amido pyrimidine compound and preparation method thereof
  • 2-amido pyrimidine compound and preparation method thereof
  • 2-amido pyrimidine compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The solvent, temperature, base and additives of the reaction system of 1,3-diyne, guanidine hydrochloride and base.

[0040]

[0041] where T refers to temperature.

[0042]

[0043] In a dry sealed tube, add solvent (2mL) and 1,3-diyne (0.2mmoL), cesium carbonate (0.4mmol) and guanidine hydrochloride (0.24-2mmol) successively, and stir the reaction at a suitable temperature (see list medium temperature item).

[0044] After the reaction was completed (monitored by thin-layer chromatography), saturated brine was added, extracted with ethyl acetate (three times in total), the organic phase was collected, and after the solvent was removed under reduced pressure, the residue was obtained by thin-layer chromatography to obtain the target product (petroleum ether, Or petroleum ether / ethyl acetate=10:1, volume ratio).

Embodiment 2

[0046] Studies on the reaction of 1,3-diyne with 10 equivalents of guanidine hydrochloride.

[0047]

[0048]

[0049]

[0050] In a dry sealed tube, dimethyl sulfoxide (2 mL), 1,3-diyne (0.2 mmol), cesium carbonate (0.4 mmol) and guanidine hydrochloride (2 mmol) were sequentially added, and the reaction was stirred at 120°C.

[0051] After the reaction is finished (monitored by thin-layer chromatography), add saturated brine, extract with ethyl acetate (three times in total), collect the organic phase, and remove the solvent under reduced pressure by thin-layer chromatography of the residue to obtain the target product (petroleum ether, or petroleum ether / ethyl acetate=10:1, volume ratio).

Embodiment 3

[0053] Studies on the reaction of 1,3-diyne with 1.2 equivalents of guanidine hydrochloride.

[0054]

[0055]

[0056] In a dry sealed tube, dimethyl sulfoxide (2 mL), 1,3-diyne (0.2 mmol), cesium carbonate (0.4 mmol), and guanidine hydrochloride (1.2 mmol) were added sequentially at 120°C and stirred for reaction.

[0057] After the reaction is finished (monitored by thin-layer chromatography), add saturated brine, extract with ethyl acetate (three times in total), collect the organic phase, and remove the solvent under reduced pressure by thin-layer chromatography of the residue to obtain the target product (petroleum ether, or petroleum ether / ethyl acetate=10:1, volume ratio).

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Abstract

The invention relates to a 2-amido pyrimidine compound and a preparation method thereof. The structural formula of the compound is shown in the specification, wherein R is selected from a benzene ring or an aryl group containing a substituent group; the aryl group is one of a phenyl group, thiophene or benzpyrole. The preparation method comprises the steps of adding an organic solvent into a dry container, then adding a 1,3-diacetylene compound, alkali and guanidine hydrochloride, and reacting under stirring for 8-12 hours at a temperature of 110-130 DEG C; after the finishing of the reaction, adding saturated salt water, extracting with an organic solvent, collecting an organic phase, and separating to obtain the target product. Compared with the prior art, the preparation method disclosed by the invention has the advantages that the reaction system is simple, the condition is mild, the substrate application range is wide, the reaction operation is convenient and rapid, the reaction yield is as high as 90-99%, the resources of raw materials are wide, the cost is low, and the chemoselectivity of the reaction can also be well regulated and controlled; and the preparation method has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a 2-aminopyrimidine compound and a preparation method thereof. Background technique [0002] Pyrimidine compounds refer to six-membered heterocyclic compounds containing two nitrogen atoms in the molecular structure, and are isomers with pyridazine and pyrazine. Due to the presence of conjugated double bonds in the molecular structure, it has a special ultraviolet spectrum. It is easily soluble in water. Its basicity is weaker than that of pyridine, and it is difficult to undergo electrophilic substitution reactions. Only bromination reactions can occur at the 5-position, and nitration cannot occur. React with sulfonation, but nucleophilic substitution is more likely to occur. Pyrimidine derivatives widely exist in nature, such as sulfadiazine, barbiturate, vitamin B1, etc. [0003] Pyrimidine derivatives are very important heterocyclic compounds. Because of their import...

Claims

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Application Information

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IPC IPC(8): C07D239/42C07D409/14C07D403/14
CPCC07D239/42C07D403/14C07D409/14
Inventor 赵晓明张亮
Owner TONGJI UNIV