CN111763196A - 一种含吡啶基嘧啶衍生物及其制备方法 - Google Patents
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- 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 26
- 125000004076 pyridyl group Chemical group 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 16
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims abstract description 8
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 claims abstract description 6
- RAFAYWADRVMWFA-UHFFFAOYSA-N 4,6-dimethyl-1h-pyrimidine-2-thione Chemical compound CC1=CC(C)=NC(S)=N1 RAFAYWADRVMWFA-UHFFFAOYSA-N 0.000 claims abstract description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 239000004570 mortar (masonry) Substances 0.000 claims abstract description 4
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- 239000000047 product Substances 0.000 claims description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 238000004440 column chromatography Methods 0.000 claims description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
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- 238000005406 washing Methods 0.000 claims description 3
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- 238000013375 chromatographic separation Methods 0.000 claims 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 4
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- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical group SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005504 styryl group Chemical group 0.000 abstract description 2
- YJVKLLJCUMQBHN-UHFFFAOYSA-N 2-pyridin-2-ylpyrimidine Chemical class N1=CC=CC=C1C1=NC=CC=N1 YJVKLLJCUMQBHN-UHFFFAOYSA-N 0.000 abstract 1
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract
本发明属于嘧啶衍生物制备技术领域,具体涉及一种含吡啶基嘧啶衍生物及其制备方法,具体的制备方法为:首先2‑巯基‑4,6‑二甲基嘧啶与NaOH水溶液混合,在冰浴条件下,向混合液内逐滴滴入溶解好的氯甲基吡啶盐酸盐,反应结束后过滤、提纯得到白色固体的中间体;然后称取中间体、4‑(2‑甲氧基乙氧基)乙基)苯甲醛和叔丁醇钾一起加入玛瑙研钵中,迅速研磨反应,溶解萃取、分离提纯后即得黄色粘稠状的目标产物,克服了现有技术的不足,以连有巯基吡啶基团的嘧啶为电子受体,以多醚链为电子给体,以苯乙烯基为共轭桥,设计合成出了吡啶基嘧啶类衍生物;原料易得,目标产物采用了无溶剂Knoevenagel方法,反应迅速,产率高。
Description
技术领域
本发明属于嘧啶衍生物制备技术领域,具体涉及一种含吡啶基嘧啶衍生物及其制备方法。
背景技术
嘧啶作为生物体必须天然碱基之一,对动植物的新陈代谢起着至关重要作用。嘧啶在医药、农药方面的应用尤其广泛。嘧啶类化合物在杀菌、抗癌、杀虫、抗病毒方面具有良好的药效作用。
嘧啶含有四个碳原子和两个氮原子构成的共轭六元杂环,其芳香性小于吡啶,四个碳原子上均能发生取代反应,生成取代嘧啶衍生物。嘧啶衍生物还是制备医药的中间体,近年来成为医药研究热门的研究领域之一。由于其是生命体中重要的物质,其较强的生物活性也一直受到人们的关注。
发明内容
本发明的目的在于提供一种含吡啶基嘧啶衍生物及其制备方法,克服了现有技术的不足,通过分子设计得到光学性质优良的含吡啶基嘧啶衍生物。
为解决上述问题,本发明所采取的技术方案如下:
一种含吡啶基嘧啶衍生物,所述含吡啶基嘧啶衍生物的结构式如下:
基于上述一种含吡啶基嘧啶衍生物的制备方法包括如下步骤:
步骤一、中间体的合成,
称取一定量的2-巯基-4,6-二甲基嘧啶与适量5mol/l的NaOH水溶液混合,在冰浴条件下,向混合液内逐滴滴入溶解好的氯甲基吡啶盐酸盐,滴加反应结束后常温反应2h,加入NaOH调节PH后滤去沉淀物,用CH2Cl2-H2O萃取,无水MgSO4干燥过夜,抽滤,洗涤,旋出CH2Cl2,柱层析分离提纯,得到白色固体的中间体;
步骤二、目标产物的合成,
称取步骤一得到的中间体、4-(2-甲氧基乙氧基)乙基)苯甲醛和叔丁醇钾,一起加入到玛瑙研钵中,迅速研磨15min,反应结束后,CH2Cl2溶解粗产物,水萃取3-5遍,无水MgSO4干燥过夜,浓缩溶剂,柱层析分离提纯,得黄色粘稠状的目标产物。
进一步,所述步骤一中2-巯基-4,6-二甲基嘧啶和氯甲基吡啶盐酸盐的摩尔比为1:2。
进一步,所述步骤一中层析分离的乙酸乙酯与石油醚体积比为1:3。
进一步,所述步骤二中加入中间体、4-(2-甲氧基乙氧基)乙基)苯甲醛和叔丁醇钾的摩尔比为1:3:2。
进一步,所述步骤二中反应过程中采用薄层色谱跟踪反应进行监控。
进一步,所述步骤二中层析分离的乙酸乙酯与石油醚体积比为1:4。
本发明与现有技术相比较,具有以下有益效果:
本发明所述一种含吡啶基嘧啶衍生物及其制备方法,以连有巯基吡啶基团的嘧啶为电子受体,以多醚链为电子给体,以苯乙烯基为共轭桥,设计合成出了吡啶基嘧啶类衍生物;原料易得,目标产物采用了无溶剂Knoevenagel方法,反应迅速,产率高;通过了系统全面的谱学表征手段确定了化合物的结构,氢谱数据显示目标产物的苯乙烯共轭桥为反式结构。
目标产物在不同的溶剂中都有较好的溶解性,其紫外吸收和单光子荧光光谱规律性强:随着溶剂极性的增大,紫外吸收光谱位移变化不明显,单光子荧光最佳发射波长出现了明显的红移;荧光量子产率随着溶剂极性增加逐渐降低;真空下的理论计算与水中测试的结果进行比较高度一致。
本发明的有益效果体现在:
1、目标产物采用了无溶剂Knoevenagel方法,反应迅速,产率高。
2、目标产物紫外吸收和单光子荧光光谱规律性强。真空下的理论计算与水中测试的结果进行比较高度一致。
3、目标产物含有吡啶基团结构,在水中的溶解度大,有利于在生物体内检测方面的应用;
4、本发明目标产物的制备是以嘧啶作原料,原料易得,成本低,合成步骤简单,产率高。
附图说明
图1是本发明目标产物的1H NMR图。
图2是本发明目标产物的13C NMR图。
图3是本发明目标产物的MOLDI-TOF图。
图4是本发明目标产物理论计算HOMO(左)and LUMO(右)图。
具体实施方式
下面将结合本发明实施例中的附图,对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
本发明所述一种含吡啶基嘧啶衍生物的结构式如下:
本实施例中含吡啶基嘧啶衍生物的制备方法如下:
1、中间体的合成
0.25g(1.8mmol)2-巯基-4,6-二甲基嘧啶和0.7mL NaOH(5M)水溶液混合在150mL圆底烧瓶中,冰浴条件下,逐滴滴入溶解好的氯甲基吡啶盐酸盐0.6g(3.6mmol),溶液呈橙红色,滴加反应结束后常温反应2h,用5M NaOH中和反应液,滤去沉淀物,CH2Cl2-H2O萃取,无水MgSO4干燥过夜,抽滤,洗涤,旋出CH2Cl2,柱层析分离提纯(石油醚:乙酸乙酯=3:1),得到白色固体的中间体0.3g。固体中间体的产率:84%。
表征:1H-NMR(400MHz,CD3COCD3):2.36(s,6H),4.54(s,2H),6.88(s,1H),7.24-7.27(t,J=6.20Hz,1H)7.52-7.54(d,J=8.00Hz,1H),7.71-7.75(t,J=8.00Hz,1H),8.54-8.55(d,J=4.00Hz,1H).13C-NMR(100MHz,CD3COCD3):23.23,36.21,39.55,115.81,122.04,123.05,136.45,149.07,157.54,166.83,169.40.MALDI–TOF–MS:m/z,232.09(M+,100%)。
2、目标产物的合成
称取0.46g(2mmol)的目标产物、1.12g(6mmol)的4-(2-甲氧基乙氧基)乙基)苯甲醛和4.8g(4.1mmol)的叔丁醇钾加入到玛瑙研钵中,迅速研磨15分钟,薄层色谱跟踪反应,反应结束后,CH2Cl2溶解粗产物,水萃取3-5遍,无水硫酸镁干燥过夜,浓缩溶剂,柱层析分离(乙酸乙酯:石油醚=1:4),得黄色粘稠状的目标产物0.58g,目标产物的产率:45%。
表征:1H NMR:(400MHz,CD3Cl),δ(ppm):3.36(s,6H),3.58~3.59(d,J=4.00Hz,8H),3.77~3.80(m,4H),3.99~4.01(m,4H),4.68(s,2H),6.82~6.86(d,J=16.00,2H),6.89~6.94(t,J=10,4H),7.11~7.19(m,2H),7.50~7.52(d,J=8.00,5H),7.78~7.82(d,J=16.00,2H),8.64~8.67(t,J=6.00,1H)13C-NMR(100MHz,CD3Cl):36.59,58.51,67.37,69.47,70.53,71.76,121.93,122.98,123.27,125.42,128.32,129.03,129.87,130.16,136.49,148.93,159.76,162.36,162.96,170.09.MALDI-TOF,m/z(%):644.29([M+H]+,100)。
试验例:
取上述方法制备的目标产物采用核磁共振氢谱(检测结果见图1)、核磁共振质谱(检测结果见图2)以及基质辅助激光解吸电离飞行时间质谱(检测结果见图3)检测确认结构。
目标产物的紫外-可见吸收光谱理论计算结果见表1:
表1紫外-可见吸收光谱理论计算结果
compd | λ<sub>cal</sub>/nm | E<sub>cal</sub>/eV | f(a.u) | Composition |
目标产物 | 384 | 2.75 | 1.7723 | (196)HOMO→(197)LUMO |
光学性质:
对目标产物在不同溶剂中的光物理性质进行试验,具体结果见表2:
表2光物理性质
根据表2的结果所示,目标产物在不同的溶剂中都有较好的溶解性,其紫外吸收和单光子荧光光谱规律性强:随着溶剂极性的增大,紫外吸收光谱位移变化不明显,单光子荧光最佳发射波长出现了明显的红移;荧光量子产率随着溶剂极性增加逐渐降低。
对于本领域技术人员而言,显然本发明不限于上述示范性实施例的细节,而且在不背离本发明的精神或基本特征的情况下,能够以其他的具体形式实现本发明。因此,无论从哪一点来看,均应将实施例看作是示范性的,而且是非限制性的,本发明的范围由所附权利要求而不是上述说明限定,因此旨在将落在权利要求的等同要件的含义和范围内的所有变化囊括在本发明内。不应将权利要求中的任何附图标记视为限制所涉及的权利要求。
Claims (7)
2.根据权利要求1所述的一种含吡啶基嘧啶衍生物的制备方法,其特征在于:包括如下步骤:
步骤一、中间体的合成,
称取一定量的2-巯基-4,6-二甲基嘧啶与适量5mol/l的NaOH水溶液混合,在冰浴条件下,向混合液内逐滴滴入溶解好的氯甲基吡啶盐酸盐,滴加反应结束后常温反应2h,加入NaOH调节PH后滤去沉淀物,用CH2Cl2-H2O萃取,无水MgSO4干燥过夜,抽滤,洗涤,旋出CH2Cl2,柱层析分离提纯,得到白色固体的中间体;
步骤二、目标产物的合成,
称取步骤一得到的中间体、4-(2-甲氧基乙氧基)乙基)苯甲醛和叔丁醇钾,一起加入到玛瑙研钵中,迅速研磨15min,反应结束后,CH2Cl2溶解粗产物,水萃取3-5遍,无水MgSO4干燥过夜,浓缩溶剂,柱层析分离提纯,得黄色粘稠状的目标产物。
3.根据权利要求2所述的一种含吡啶基嘧啶衍生物的制备方法,其特征在于:所述步骤一中2-巯基-4,6-二甲基嘧啶和氯甲基吡啶盐酸盐的摩尔比为1:2。
4.根据权利要求2所述的一种含吡啶基嘧啶衍生物的制备方法,其特征在于:所述步骤一中层析分离的乙酸乙酯与石油醚体积比为1:3。
5.根据权利要求2所述的一种含吡啶基嘧啶衍生物的制备方法,其特征在于:所述步骤二中加入中间体、4-(2-甲氧基乙氧基)乙基)苯甲醛和叔丁醇钾的摩尔比为1:3:2。
6.根据权利要求2所述的一种含吡啶基嘧啶衍生物的制备方法,其特征在于:所述步骤二中反应过程中采用薄层色谱跟踪反应进行监控。
7.根据权利要求2所述的一种含吡啶基嘧啶衍生物的制备方法,其特征在于:所述步骤二中层析分离的乙酸乙酯与石油醚体积比为1:4。
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