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A kind of 2-amino pyrimidine compound and preparation method thereof

An aminopyrimidine and compound technology, applied in the field of 2-aminopyrimidine compounds and their preparation, can solve the problems of low efficiency, many reaction steps, harsh reaction conditions and the like, and achieves low cost, mild conditions and simple reaction system. Effect

Inactive Publication Date: 2017-05-24
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of 2-amino pyrimidine compound and preparation method thereof
  • A kind of 2-amino pyrimidine compound and preparation method thereof
  • A kind of 2-amino pyrimidine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Research on solvent, temperature, alkali and additives of 1,3-diacetylene, guanidine hydrochloride and alkali reaction system.

[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), and stir the reaction at a suitable temperature (see table Medium temperature item).

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

Embodiment 2

[0046] Study on the reaction of 1,3-diacetylene and 10 equivalents of guanidine hydrochloride.

[0047]

[0048]

[0049]

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

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

Embodiment 3

[0053] Study on the reaction of 1,3-diacetylene and 1.2 equivalents of guanidine hydrochloride.

[0054]

[0055]

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

[0057] After the reaction is over (monitored by thin-layer chromatography), saturated brine is added, extracted with ethyl acetate (three times in total), the organic phase is collected, the solvent is removed under reduced pressure, and the residue is thin-layer chromatography 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, which are isomers with pyridazine and pyrazine. Due to the presence of conjugated double bonds in the molecular structure, it has a special ultraviolet spectrum and is easily soluble in water. Its basicity is weaker than that of pyridine. It is difficult to undergo electrophilic substitution reactions. Only the 5-position can undergo bromination reaction, but not nitration. It reacts with sulfonation, but is prone to nucleophilic substitution. Pyrimidine derivatives are widely found in nature, such as sulfadiazine, barbital, vitamin B1, etc. [0003] Pyrimidine derivative is a very important heterocyclic compound. Because of its important biological activity and cu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/42C07D409/14C07D403/14
CPCC07D239/42C07D403/14C07D409/14
Inventor 赵晓明张亮
Owner TONGJI UNIV