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Preparation method of novel electrophilic reagent-pyrimidine methanesulfonate

A technology of pyrimidine mesylate and hydroxypyrimidine, which is applied in the field of preparation of new electrophilic pyrimidinyl mesylate, can solve the problems that the synthesis method of new electrophile pyrimidinyl mesylate has not been reported in the literature, and achieves the goal of preparing Simple process, high yield, easy access to raw materials

Inactive Publication Date: 2018-12-25
GANSU AGRI UNIV
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Problems solved by technology

At present, various aryl methanesulfonates have been successfully prepared and successfully used in Stille [11] ,Suzuki [12] , Hiyama [13] ,Kumada [14] and Sonogashira [15] etc., but the research on the synthetic method of the new electrophile pyrimidine mesylate has not been reported in the literature yet.

Method used

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  • Preparation method of novel electrophilic reagent-pyrimidine methanesulfonate
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  • Preparation method of novel electrophilic reagent-pyrimidine methanesulfonate

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[0020] The invention provides a method for preparing pyrimidine mesylate represented by formula (1), the method comprising: using 2-hydroxypyrimidine and methanesulfonyl chloride represented by formula (2) as reaction raw materials, and using alkali as binding agent Acid agent, reacts in organic solvent, prepares pyrimidine mesylate,

[0021]

[0022] Among them, R 1 C1-C5 alkyl, R 2 is H, X, C1-C5 alkyl or C1-C5 alkoxy, and OMs is methylsulfonic acid group.

[0023] In a specific embodiment, R 1 is methyl (Me), ethyl, propyl, butyl or pentyl. In the preferred case, R 1 is methyl or ethyl.

[0024] In a specific embodiment, R 2 is H, F, Cl, Br, methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, butoxy or pentyloxy. In the preferred case, R 2 for H, Cl, CH 3 or OCH 3 .

[0025] In a specific embodiment, the structural formula of pyrimidine mesylate shown in formula (1) is as follows:

[0026]

[0027]

[0028] In the method of the present inven...

Embodiment 1-8

[0038] Add 2.0mmol of 2-hydroxypyrimidine represented by formula (2), 4.0mmol of methanesulfonyl chloride and 10mL of dichloromethane into a 50mL round bottom flask, and slowly add 10.0mmol of Et 3 N, the temperature was raised to room temperature and stirred for 2 h, and TLC detected that the reaction was complete. Transfer the reaction solution into a separatory funnel, add 10mL of water, vibrate and stand to separate layers, collect the lower organic phase, evaporate the solvent under reduced pressure, and recrystallize the obtained crude product with ethanol to obtain pyrimidine mesylate.

[0039] Wherein, the corresponding group in the 2-hydroxypyrimidine shown in the formula (2) that adopts in each embodiment and the pyrimidine mesylate shown in the prepared formula (1) and the yield of target product pyrimidine mesylate As shown in Table 1 below.

[0040] Table 1

[0041]

[0042]

[0043] The structural formulas of the target products prepared in Examples 1-8 a...

Embodiment 1

[0048] The characterization data of the target product prepared in Example 1 are as follows: colorless crystals, mp: 96-98°C, yield: 87.2%; 1 H NMR (600MHz, CDCl 3 ):δ7.65(d,J=7.2Hz,2H),7.52-7.44(m,3H),4.21(q,J=7.2Hz,2H),3.57(s,3H),2.63(s,3H) ,1.07(t,J=7.2Hz,3H). 13 C NMR (150MHz, CDCl 3 ): δ169.87, 166.96, 166.92, 158.68, 136.25, 130.90, 128.69, 128.43, 124.30, 62.24, 41.00, 22.64, 13.57.

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Abstract

The invention relates to the technical field of organic synthesis technology, in particular to a preparation method of novel electrophilic reagent-pyrimidine methanesulfonate. The preparation method includes subjecting raw materials, namely 2-hydroxypyrimidine as shown in the formula (2) and methylsulfonyl chloride, and an acid-binding agent, namely alkali to reaction in an organic solvent to obtain pyrimidine methanesulfonate. The preparation method can realize synthesis of pyrimidine methanesulfonate simply and has high yield of pyrimidine methanesulfonate.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a novel electrophile pyrimidine mesylate. Background technique [0002] Coupling reactions catalyzed by transition metals are effective methods for constructing C-C, C-N, C-S bonds, etc. in organic synthesis [1-4] , with the help of coupling reaction, the two types of groups can be stacked to form a new organic molecular structure with potential biological activity. In classical coupling reactions, organohalides exhibit high reactivity and are the most commonly used electrophiles [5-7] . With the continuous and in-depth research on coupling reactions, it has been found that organic halides are difficult to prepare, have many reaction by-products, and pollute the environment in use. The further development of the reaction is of great significance. [0003] In recent years, various types of sulfonate, phosphonate, and pivalate based on phenolic...

Claims

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Application Information

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IPC IPC(8): C07D239/34
CPCC07D239/34
Inventor 巩海鹏徐玉梅崔彦君
Owner GANSU AGRI UNIV
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