| 第 53 卷第 3 期 |  | Vol. 53 No. 3 | | 2023 年 6 月 | Jun 2023 |
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所屬欄目：醫藥及中間體
（3，5，6-三甲基吡嗪-2-基）甲胺的合成 |
| 徐小娜1，張 婧1，王曉霞1，仝紅娟2，朱周靜2
（1. 咸陽(yáng)職業(yè)技術(shù)學(xué)院 醫藥化工學(xué)院，陜西 咸陽(yáng) 712000；2. 咸陽(yáng)市分子影像與藥物合成重點(diǎn)實(shí)驗室 陜西國際商貿學(xué)院醫藥學(xué)院，陜西 咸陽(yáng) 712046） |
| 摘 要：報道一種川芎嗪衍生物（3，5，6-三甲基吡嗪-2-基）甲胺的合成方法。以（3，5，6-三甲基吡嗪-2-基）甲醇（2）為原料，與疊氮磷酸二苯酯（DPPA）反應得到2-疊氮甲基-3，5，6-三甲基吡嗪（3），再經(jīng)鈀/碳加氫還原得到目標化合物。產(chǎn)物及中間體結構經(jīng)1H NMR、13C NMR、IR和ESI-MS表征確證。結果表明，疊氮化反應的優(yōu)化條件為n（DPPA）∶n（2）=1.2∶1.0、反應溫度25 ℃、反應時(shí)間5 h，還原反應的優(yōu)化條件為反應溶劑甲醇、鈀碳用量為3質(zhì)量的10%、反應時(shí)間1 h。 |
| 關(guān)鍵詞：川芎嗪衍生物；疊氮化反應；還原反應 |
| 中圖分類(lèi)號：TQ463 文獻標識碼：A 文章編號：1009-9212（2023）03-0027-03 |
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| Synthesis of (3,5,6-Trimethylpyrazin-2-yl)methanamine |
| XU Xiao-na1, ZHANG Jing1, WANG Xiao-xia1, TONG Hong-juan2, ZHU Zhou-jing2
(1. School of Pharmaceutical & Chemical Engineering, Xianyang Vocational Technical College, Xianyang 712000, China; 2. Xianyang Key Laboratory of Molecular Imaging and Drug Synthesis, School of Pharmacy, Shaanxi Institute of International Trade & Commerce, Xianyang 712046, China) |
| Abstract：The process for the synthesis of Ligustrazine derivative (3,5,6-trimethylpyrazin-2-yl)methanamine was reported. The intermediate 2-azide methyl-3,5,6-trimethylpiperazine (3) was obtained from the reaction of (3,5,6-trimethylpyrazin-2-yl)methanol (2) with DPPA. Then, the target compound was obtained through Pd/C hydroreduction. The structure of the product and intermediate were characterized by 1H NMR, 13C NMR, IR and ESI-MS. The reaction conditions were investigated and found that the optimum conditions for azide reaction were as followings: the ratio of n(DPPA)∶n(2) at 1.2∶1.0, the reaction time of 5 h at 25 ℃. The optimum conditions for reduction reaction were as following: methanol as the reaction solvent, 10% of the mass of 3 as the dosage of Pd/C, and the reaction time of 1 h. |
| Key words：Ligustrazine derivatives; azide reaction; reduction reaction |
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基金項目：陜西省自然科學(xué)基礎研究計劃（面上）項目（2022JM-561），咸陽(yáng)職業(yè)技術(shù)學(xué)院博士科研基金項目（2021BK01），陜西國際商貿學(xué)院“中藥藥效物質(zhì)研究”創(chuàng )新團隊資助項目（SSY18TD02）。
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作者簡(jiǎn)介：徐小娜（1985—），女，講師，博士，研究方向：天然產(chǎn)物結構修飾、有機合成及工藝、藥物分子設計合成及活性研究（E-mail:xuxiaona@163.com）。
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收稿日期：2023-04-23
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