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Triazolopyrimidine compound and preparation method thereof

A technology for azolopyrimidines and compounds is applied in the field of preparation of triazolopyrimidine compounds and can solve problems such as low yield of active components

Active Publication Date: 2011-08-17
北京颖泰嘉和分析技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] An object of the present invention is to overcome the disadvantages of low yields of active ingredients of triazolopyrimidine herbicides prepared by existing methods, and provide a triazolopyrimidine compound and a method for preparing a triazolopyrimidine compound

Method used

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  • Triazolopyrimidine compound and preparation method thereof
  • Triazolopyrimidine compound and preparation method thereof
  • Triazolopyrimidine compound and preparation method thereof

Examples

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preparation example Construction

[0041] According to the second aspect of the present invention, the present invention also provides a method for preparing a triazolopyrimidine compound having a general formula as shown in formula (2), the method comprising: under cyclization reaction conditions, an organic base and Under the existence of hydrogen peroxide, make the compound and carbon disulfide contact reaction of general formula shown in formula (3);

[0042]

[0043] Formula (2)

[0044] Among them, R 1 for C 1 -C 4 the alkyl group; R 2 and R 3 are the same or different, and each independently selected from hydrogen, halogen, C 1 -C 4 Alkyl or -OR 5 , where R 5 for C 1 -C 4 of alkyl. Preferably, R 1 is methyl or ethyl; R 2 and R 3 are the same or different, and are each independently selected from fluorine, chlorine, methyl, ethyl, methoxy or ethoxy. Further preferably, R 1 is methyl or ethyl; R 2 and R 3 one of which is fluorine or chlorine and the other is hydrogen, methyl or ethyl; ...

Embodiment 1

[0075] This example is used to illustrate the triazolopyrimidine compound and its preparation method provided by the present invention.

[0076] Add 166g of 2,4-dichloro-5-fluoropyrimidine (purchased from Chengdu Yuyang High-tech Development Co., Ltd.) and 154g of sodium methyl mercaptide to a 1L flask, and react at 70°C for 6 hours. Then, 237 g of methanol and 294 g of hydrazine hydrate were added thereto, and reacted at 70° C. for 7 hours. The resulting mixture was cooled to 5 °C and the solid was collected by vacuum filtration, washed with 150 mL of cold methanol, and dried to a stable weight to give 149 g of a white solid material with a melting point of 146 °C, NMR data Such as: 1 H-NMR (500MHz DMSO) δ: 2.55 (s, 3H), 4.71 (d, 2H), 8.15 (s, 1H), 8.45 (t, 1H); mass spectrometry data such as: MS (m / z) 175 ( +H + ), 197 (+Na + ). From this, it was confirmed that the solid substance was 5-fluoro-4-hydrazino-2-methylthiopyrimidine, its purity was 98% by weight, and its yie...

Embodiment 2

[0080] This example is used to illustrate the triazolopyrimidine compound and its preparation method provided by the present invention.

[0081] Add 182.5g of 2,4,5-trichloropyrimidine (purchased from Shanghai Yitai Technology Co., Ltd.) and 185g of sodium ethanethiolate into a 1L flask, contact and react at 100°C for 10 hours, and then add 237 g of methanol and 294 g of hydrazine hydrate were added and reacted at 70° C. for 7 hours. The resulting mixture was cooled to 5 °C and the solid was collected by vacuum filtration, washed with 150 mL of cold methanol, and dried to a stable weight to give 191 g of a white solid material with a melting point of 120 °C, NMR data Such as: 1 H-NMR (500MHz DMSO) δ: 1.32 (t, 3H), δ: 2.98 (dd, 2H), 4.64 (d, 2H), 7.77 (s, 1H), 8.69 (t, 1H); mass spectrometry data such as : MS(m / z)205(+H + ), 227(+Na + ). From this, it was confirmed that the solid substance was 5-chloro-4-hydrazino-2-ethylthiopyrimidine, its purity was 98% by weight, and it...

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Abstract

The invention provides a triazolopyrimidine compound shown as a formula (1) and a preparation method thereof as well as a method for preparing a compound shown as a formula (5) by adopting the triazolopyrimidine compound. The method for preparing the compound shown as the formula (5) comprises the following steps that: the triazolopyrimidine compound and a compound with a general formula R1'-ONa undergo contact reaction under the condition of rearrangement reaction. In the formula (1), R1 is alkyl of C1-C4; R2 and R3 are same or different and are independently selected from hydrogen, halogen,alkyl of C1-C4 or -OR5; R5 is alkyl of C1-C4; and R4 is hydrogen, benzyl or alkyl of C1-C4. In the formula (5), R1' is alkyl of C1-C4; R2 and R3 are same or different and are independently selected from hydrogen, halogen, alkyl of C1-C4 or -OR5; R5 is alkyl of C1-C4; and R4' is benzyl or alkyl of C1-C4. The two compounds are shown as the formula (1) and the formula (5).

Description

technical field [0001] The invention relates to a triazolopyrimidine compound and a preparation method of the triazolopyrimidine compound. Background technique [0002] Triazolopyrimidine herbicides are a new class of super-efficient herbicides discovered by Dow Chemical Company after sulfonylurea and imidazolinone herbicides. Its activity is equivalent to that of sulfonylurea herbicides, and the dosage is about Its target is still acetolactate synthase (ALS). [0003] Cloransulam-methyl, diclosulam and florasulam all belong to the active ingredients of triazolopyrimidine herbicides, and their general chemical formula is as follows (6 ) as shown: [0004] [0005] Formula (6) [0006] Among them, R 1 ″ for CH 3 or C 2 h 5 ; 2 ' and R 3 ' each F, Cl, Br, CH 3 、C 2 h 5 , OCH 3 、OC 2 h 5 or H, R 5 'is benzyl or C 2 -C 4 of alkyl. [0007] Its synthesis process has been reported, for example, WO9512595A1 discloses the method for preparing the compound shown...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 罗进超常富荣黄祯宝路凤奇吴国林李俊卿谭徐林乔振
Owner 北京颖泰嘉和分析技术有限公司
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