CN104892581B - 2-methyl-4-amino-5-(substituted-1,2,3-triazolyl)methylpyridine derivatives having bactericidal activity, and preparation method and application thereof - Google Patents

2-methyl-4-amino-5-(substituted-1,2,3-triazolyl)methylpyridine derivatives having bactericidal activity, and preparation method and application thereof Download PDF

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CN104892581B
CN104892581B CN201410082965.XA CN201410082965A CN104892581B CN 104892581 B CN104892581 B CN 104892581B CN 201410082965 A CN201410082965 A CN 201410082965A CN 104892581 B CN104892581 B CN 104892581B
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贺红武
王威
贺军波
张�林
朱国中
郭新娟
邹鹏
谭效松
彭浩
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Huazhong Normal University
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Abstract

The invention discloses 2-methyl-4-amino-5-(substituted-1,2,3-triazolyl)methylpyridine derivatives having a bactericidal activity, and a preparation method and an application thereof, wherein the derivatives have the structural formula described in the specification, wherein R＜1＞ represents H or I, X represents O, NH or S, Y represents benzoylamide thiocarbonyl or substituted benzoylamide thiocarbonyl, 2-phenyl-1,3,4-thiadiazole(oxadiazole)-5-yl or 2-substituted phenyl-1,3,4-thiadiazole(oxadiazole)-5-yl, benzophenone (acetophenone) imine or substituted benzophenone (acetophenone) imine, and Y-involved substituents on a benzene ring mainly comprise H, halogen, nitro, cyano group, CF3, C1-4 alkyl, methoxyl, C1-2 carboxylic group or carboxylate group. The compounds have a significant control effect on wheat gibberellic hypha, rice rhizoctonia solani, cucumber borrytis cinerea, tomato alternaria solani, alternaria alternata and cucumber colletrichum orbiculare, and can be used for bactericidal active ingredients.

Description

There is 2- methyl -4- amino -5- (replacing -1,2,3- triazolyl) first of bactericidal activity Yl pyrimidines derivant, its preparation method and application
Technical field
The present invention relates to 2- methyl -4- amino -5- (replacing -1,2,3- triazolyl) methylpyrimidine derivant, its preparation side Method and its application.
Background technology
Pyruvate dehydrogenase system be biological energy i (in vivo) metabolic regulation during the important enzyme system of a class, it is connected to sugared ferment The conversion of pyruvate that solution obtains is the process of the substrate acetyl coenzyme A of tricarboxylic acid cycle.Based on its important Biochemical Characteristics, acetone Acidohydrogenase system can be studied as pesticide target completely.In recent years, the present inventor is with pyruvate dehydrogenase system in microorganism For target, design and synthesized the new structure compound having as antibacterial using value.For example, A class（He Hongwu etc., in State's patent of invention, Application No. 201110268908.7）Compound then shows excellent bactericidal activity.
Content of the invention
It is an object of the invention to explore that there is the new compound of bactericidal activity, and provide one kind there is bactericidal activity 2- methyl -4- amino -5- (replace -1,2,3- triazolyl) methylpyrimidine derivant, its preparation method and application.
The present invention optimizes the structure type of Y further it is proposed that one kind has bactericidal activity on the basis of A class compound New compound, it has formula（I）Structure：
Wherein, R1Represent hydrogen or I；X represents O, NH or S；Y represents Benzoylamide thiocarbonyl group or substituted benzamide thion Base, 2- phenyl -1,3,4- thiophene（?）Diazole -5- base or 2- substituted-phenyl -1,3,4- thiophene（?）- 5- base, benzene first（Ethyl ketone）Imines Base or substituted benzoyl（Ethyl ketone）Imido grpup；The substituent group on phenyl ring involved by Y is mainly：H, halogen, nitro, cyano group, CF3、C1-4Alkyl, methoxyl group, C1-2Carboxylic acid group or carboxylic acid ester groups；Monosubstituted on phenyl ring optional position of substituent group or take more In generation, substituent group is identical or different.
Compound（I）Including with formula（I-1）[the 1- representing（2- methyl -4- aminopyrimidine -5- methyl）-1H-1,2,3- Triazole] -4- methyl -（Substituted benzoyl）Thiocarbamate（Thiourea）Compound, with formula（I-2）The N- representing（（1- （（2- methyl -4- aminopyrimidine -5- base）Methyl）- 1H-1,2,3- triazole-4-yl）Methyl）- 2- substituted-phenyl -1,3,4- thiophene （?）- 5- base sulfide compound, with formula（I-3）O- [the 1- representing（2- methyl -4- aminopyrimidine -5- methyl）-1H-1,2, 3- triazole-4-yl] substituted benzoyl（Ethyl ketone）Oxime ether compound.
Formula proposed by the invention（I-1）, formula（I-2）, formula（I-3）Compound structure be not reported, lead to Formula（I-1）, formula（I-2）, formula（I-3）Structure be defined respectively as：
Formula（I-1）In, X is oxygen or NH；R1Definition and formula（I）R1Define identical；R2For：H, halogen, nitro, Methoxyl group or C1-4Alkyl；R3For：H, halogen, nitro, cyano group, CF3、C1-4Alkyl or methoxyl group；R2With R3Position is interchangeable.
Formula（I-2）In, X is oxygen or S；R1Definition and formula（I）R1Define identical；R2For：H, halogen, nitro or C1-4Alkyl；R3For：H, halogen, nitro, CF3, methoxyl group or C1-4Alkyl；R2With R3Position is interchangeable.
Formula（I-3）In, R1Definition and formula（I）R1Define identical；R2For H, nitro or halogen；R3For：H, halogen Element, nitro, C1-4Alkyl or methoxyl group；R2With R3Position is interchangeable；R4For H or methyl.
The present invention has formula（I）The compound of structure is to fusarium graminearum, Rhizoctonia solani Kuhn, gray mold of cucumber Bacterium, tomato early blight bacterium, tobacco brown spot pathogen and cucumber anthracnose have significant preventive effect, can be used as the activity one-tenth of antibacterial Point.
There is formula（I-1）The preparation method of the compound of structure, is in catalyst and organic base or only in catalyst In the presence of, make compound（II）With alkynes intermediate（III）At a temperature of -10～80 DEG C, reaction 12-24 hour cyclization generates, A method. Reaction equation is as follows：
Above-mentioned reaction equation（1）In, formula（III）Middle R1、R2、R3, the definition of X and formula（I-1）Middle R1、R2、R3, the determining of X Justice is identical.
In above-mentioned A method reaction, compound（II）, intermediate（III）, the mol ratio of catalyst and organic base be 1：（0.8- 1.2）：（0.01-0.15）：2；Reaction dissolvent adopts organic solvent：Dichloromethane, dioxane, dichloroethanes, acetone, tertiary fourth Alcohol, water, benzene, ethyl acetate, oxolane, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide；Catalyst is：CuI、 CuBr(PPh3)3、CuSO4·5H2O:Sodium ascorbate, CuBr or Cu (OAc)2；Organic base is：Triethylamine, diisopropyl ethyl Amine, pyridine or hexahydropyridine.
There is formula（I-2）The preparation method of the compound of structure, is in catalyst and organic base or only in catalyst In the presence of, make compound（II）With intermediate（IV）At a temperature of -10～80 DEG C, reaction 12-24 hour cyclization generates, B method.Instead Answer formula as follows：
Above-mentioned reaction equation（2）In, formula（IV）Middle R1、R2、R3, the definition of X and formula（I-2）Middle R1、R2、R3, the definition of X Identical.
In above-mentioned B method reaction, compound（II）, intermediate（IV）, the mol ratio of catalyst and organic base be 1：（0.8- 1.2）：（0.01-0.15）：2；Reaction dissolvent adopts organic solvent：Dichloromethane, dioxane, dichloroethanes, acetone, tertiary fourth Alcohol：Water, benzene, ethyl acetate, oxolane, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide；Catalyst is：CuI、 CuBr(PPh3)3、CuSO4·5H2O:Sodium ascorbate, CuBr or Cu (OAc)2；Organic base is：Triethylamine, diisopropyl second Base amine, pyridine or hexahydropyridine.
There is formula（I-2）The preparation method of the compound of structure, is in catalyst and organic base or only in catalyst In the presence of, make compound（II）With intermediate（V）At a temperature of -10～80 DEG C, reaction 12-24 hour cyclization generates, C method.Reaction Formula is as follows：
Above-mentioned reaction equation（3）In, formula（V）Middle R1、R2、R3、R4Definition and formula（I-3）Middle R1、R2、R3、R4Definition Identical.
In above-mentioned C method reaction, compound（II）, intermediate（V）, the mol ratio of catalyst and organic base be 1：（0.8- 1.2）：（0.01-0.15）：2；Reaction dissolvent adopts organic solvent：Dichloromethane, dioxane, dichloroethanes, acetone, tertiary fourth Alcohol：Water, benzene, ethyl acetate, oxolane, acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide；Catalyst is：CuI、 CuBr(PPh3)3、CuSO4·5H2O:Sodium ascorbate, CuBr or Cu (OAc)2；Organic base is：Triethylamine, diisopropyl second Base amine, pyridine or hexahydropyridine.
Specific embodiment
Specifically describe the compounds of this invention below by embodiment（I）, including compound（I-1）、（I-2）、（I-3）'s Preparation method, only the present invention will be described for these embodiments, rather than limits the invention.
The compound adopting in following embodiments（II）The method described in document 1 that can be found in is prepared.
Embodiment 1：Intermediate III -1Preparation
0.28g propargyl alcohol is added in equipped with drying tube, cryogenic thermometer, the 100mL three-necked bottle of constant pressure funnel （5mmol）, 0.5g triethylamine（5mmol）With 10mL acetonitrile, cryogenic thermostat reactive bath technique is cooled to 4 DEG C, is slowly added to 10mL Benzoyl isothiocyanate acetonitrile solution, wherein benzoyl isothiocyanate be 5mmol；Reacting liquid temperature is maintained to be less than 5 DEG C, after the acetonitrile solution dropwise of benzoyl isothiocyanate finishes, it is transferred to room temperature reaction, TLC（Thin layer chromatography）Monitoring.Instead After should terminating, successively with 5% dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated common salt water washing to solution in neutrality.Then with two Chloromethanes（15mL × 3 time）Aqueous phase extracted, through merge organic faciess, anhydrous sodium sulfate drying overnight, sucking filtration, filtrate concentrate obtain final product thick Product, through silica gel column chromatography gradient elution（Petroleum ether：Ethyl acetate=3:1）Obtain final product sterling.
R1、R2、R3, X be other substituent groups intermediate III by intermediate III -1 similar approach be obtained.
Embodiment 2：Intermediate compound IV -1Preparation
5- phenyl -1,3,4- thiadiazoles -2- mercaptan, the 4.0mmol potassium carbonate of 4.0mmol is added in 50mL round-bottomed flask Powder, is dissolved in 15mL and is dried under dimethyl sulfoxide, room temperature and be added dropwise to 4.8mmol bromopropyl alcohol, stirring reaction at room temperature, TLC（Thin Layer chromatography）Monitoring reaction disappears to raw material point, after stopped reaction, system is poured in 100mL water, is sufficiently stirred for, and has solid in a large number Body separates out, and sucking filtration obtains crude product IV-1, need not purify.
R1、R2、R3, X be other substituent groups intermediate compound IV by intermediate compound IV -1 similar approach be obtained.
Embodiment 3：Intermediate V-1Preparation
Respectively 5mmol benzaldoxime, 5mmol propargyl bromide are dissolved in 20mL anhydrous acetonitrile, are subsequently adding 5mmol hydroxide Sodium, back flow reaction 8 hours, TLC（Thin layer chromatography）Monitoring reaction is completely.Acetonitrile is removed under reduced pressure, then successively through dilute hydrochloric acid, saturation Sodium bicarbonate solution, saturated common salt water washing, use ethyl acetate（20mL × 3 time）Aqueous phase extracted, through merging organic faciess, anhydrous sulfur Sour sodium is dried, and is concentrated to give crude product, acetone recrystallization obtains intermediate V-1.
R1、R2、R3、R4For other substituent groups intermediate V press intermediate V-1 similar approach be obtained.
Embodiment 4：Compound 1Preparation
By 1mmol2- methyl -4- amino -5- azido-methyl pyrimidine and the thio first of 1mmol O- propinyl benzoyl-amido Acid esters is dissolved in 20mL oxolane, adds 2mmol triethylamine and 0.1mmol Hydro-Giene (Water Science). CuI, in 60-70 DEG C of stirring reaction 10-15 hour, TLC（Thin layer chromatography）Monitoring reaction to complete, add water and has solid to separate out, through filtration under diminished pressure, washing, drying thick Product.With DMF and water recrystallization, obtain the target compound of yellow solid, yield 88%, mp：120-122 ℃.
Elementary analysiss/%：Value of calculation：C,53.25;H,4.47;N,25.57;S,8.36;Measured value：C,53.09;H, 4.74;N,25.33;S,8.04;1H NMR(400MHz,CDCl3):δ2.49(s,3H,CH3),5.35(s,2H,CH2),5.44 (s,2H,CH2),5.66(s,2H,NH2),7.41-8.03(m,5H,Ar-H),7.72(s,1H,CH),8.19(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ25.2,46.9,57.9,108.2,125.0,128.8,129.2,133.5,142.0, 156.4,161.6,165.5,167.2,179.3.IR(KBr):1277(C=S),1702(C=O),3150(N-H),3512cm-1.ESI-MS(m/z):384(M++1).
Compound 2-20 presses compound 1 similar approach and is obtained, and Structural Identification data is as follows：
Compound 2
Gained sterling is yellow solid, yield 87%, m.p.115-116 DEG C;.Elementary analysiss/%：Value of calculation：C,48.86; H,3.86;N,23.46;S,7.67;Measured value：C,48.83;H,4.20;N,23.57;S,7.82;1H NMR(400MHz, CDCl3):δ2.50(s,3H,CH3),5.36(s,2H,CH2),5.45(s,2H,CH2),5.58(s,2H,NH2),7.28-7.85 (m,4H,Ar-H),7.46(s,1H,CH),8.19(s,1H,CH).IR(KBr):1265(C=S),1717(C=O),3145(N- H),3544cm-1.ESI-MS(m/z):418(M++1).
Compound 3
Gained sterling is yellow solid, yield 84%, m.p.139-141 DEG C.Elementary analysiss/%：Value of calculation：C,48.86;H, 3.86;N,23.46;S,7.67;Measured value：C,49.24;H,3.96;N,23.53;S,7.74;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.38(s,2H,CH2),5.44(s,2H,CH2),5.66(s,2H,NH2),7.35-7.99(m,4H, Ar-H),7.72(s,1H,CH),8.05(s,1H,CH).IR(KBr):1270(C=S),1722(C=O),3147(N-H), 3454cm-1.ESI-MS(m/z):418(M++1).
Compound 4
Gained sterling is yellow solid, yield 78%, m.p.124-125 DEG C.Elementary analysiss/%：Value of calculation：C,48.86;H, 3.86;N,23.46;S,7.67;Measured value：C,49.02;H,4.05;N,23.33;S,7.75;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.43(s,2H,CH2),5.63(s,2H,NH2),7.39-7.97(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ25.2,46.8,58.1, 108.2,125.0,128.1,131.0,138.4,141.7,156.3,161.5,164.6,167.6,180.3.IR(KBr): 1277(C=S),1708(C=O),3110(N-H),3452cm-1.ESI-MS(m/z):418(M++1).
Compound 5
Gained sterling is light yellow solid, yield 73%, m.p.156-157 DEG C.Elementary analysiss/%：Value of calculation：C,54.39; H,4.82;N,24.67;S,8.07;Measured value：C,54.69;H,4.99;N,24.65;S,7.62;1H NMR(400MHz, CDCl3):δ2.49(s,3H,CH3),2.62(s,3H,CH3),5.36(s,2H,CH2),5.41(s,2H,CH2),5.67(s,2H, NH2),7.22-7.96(m,4H,Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1702 (C=O),3150(N-H),3512cm-1.ESI-MS(m/z):398(M++1).
Compound 6
Gained sterling is yellow solid, yield 83%, m.p.123-125 DEG C.Elementary analysiss/%：Value of calculation：C,54.39;H, 4.82;N,24.67;S,8.07;Measured value：C,54.17;H,4.73;N,23.55;S,8.01;1H NMR(400MHz,CDCl3): δ2.51(s,3H,CH3),2.65(s,3H,CH3),5.38(s,2H,CH2),5.43(s,2H,CH2),5.54(s,2H,NH2), 7.32-7.93(m,4H,Ar-H),7.71(s,1H,CH),8.08(s,1H,CH).IR(KBr):1253(C=S),1709(C=O), 3118(N-H),3452cm-1.ESI-MS(m/z):398(M++1).
Compound 7
Gained sterling is light yellow solid, yield 71%, m.p.146-148 DEG C.Elementary analysiss/%：Value of calculation：C,50.87; H,4.02;N,24.43;S,7.99;Measured value：C,51.04;H,4.29;N,24.32;S,7.66;1H NMR(400MHz, CDCl3):δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.46(s,2H,CH2),5.60(s,2H,NH2),7.11-7.93 (m,4H,Ar-H),7.52(s,1H,CH),8.20(s,1H,CH).IR(KBr):1253(C=S),1729(C=O),3148(N- H),3453cm-1.ESI-MS(m/z):402(M++1).
Compound 8
Gained sterling is yellow solid, yield 76%, m.p.132-133 DEG C.Elementary analysiss/%：Value of calculation：C,50.87;H, 4.02;N,24.43;S,7.99;Measured value：C,50.92;H,4.34;N,24.40;S,7.80;1H NMR(400MHz,CDCl3): δ2.50(s,3H,CH3),5.36(s,2H,CH2),5.43(s,2H,CH2),5.62(s,2H,NH2),7.07-8.06(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1253(C=S),1721(C=O),3111(N-H), 3454cm-1.ESI-MS(m/z):402(M++1).
Compound 9
Gained sterling is yellow solid, yield 70%, m.p.134-136 DEG C.Elementary analysiss/%：Value of calculation：C,44.16;H, 3.49;N,21.21;S,6.94;Measured value：C,44.44;H,3.77;N,31.38;S,6.84;1H NMR(400MHz,CDCl3): δ2.50(s,3H,CH3),5.36(s,2H,CH2),5.45(s,2H,CH2),5.61(s,2H,NH2),7.33-7.80(m,4H, Ar-H),7.66(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1721(C=O),3145(N-H), 3453cm-1.ESI-MS(m/z):463(M++1).
Compound 10
Gained sterling is yellow solid, yield 77%, m.p.141-142 DEG C.Elementary analysiss/%：Value of calculation：C,48.68;H, 3.60;N,23.38;S,7.65;Measured value：C,48.32;H,3.86;N,23.62;S,7.54;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.42(s,2H,CH2),5.59(s,2H,NH2),6.92-7.71(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1265(C=S),1725(C=O),3139(N-H), 3440cm-1.ESI-MS(m/z):420(M++1).
Compound 11
Gained sterling is yellow solid, yield 50%, m.p.73-75 DEG C.Plain analysis/%：Value of calculation：C,44.11;H, 3.27;N,24.21;S,6.93;Measured value：C,44.25;H,3.42;N,24.22;S,6.82;1H NMR(600MHz,DMSO- d6):δ2.29(s,3H,CH3),5.44(s,2H,CH2),5.49(s,2H,CH2),6.98(s,2H,NH2),7.99-8.27(m, 3H,Ar-H),8.38(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ25.3,46.8,109.3,122.4,125.2, 125.5,132.0,132.6,135.4,141.1,142.9,149.4,156.2,161.4,163.5,194.5.IR(KBr): 1243(C=S),1603(C=O),3369(N-H)cm-1.EI-MS(m/z,%):462(M+,2).
Compound 12
Gained sterling is yellow solid, yield 56%, m.p.62-64 DEG C.Elementary analysiss/%：Value of calculation：C,45.14;H, 3.34;N,21.68;S,7.09;Measured value：C,45.25;H,3.56;N,21.95;S,7.25;1H NMR(600MHz,DMSO- d6):δ2.30(s,3H,CH3),5.38(s,2H,CH2),5.47(s,2H,CH2),6.98(s,2H,NH2),7.53-7.81(m, 3H,Ar-H),8.25(s,1H,CH).IR(KBr):1245(C=S),1604(C=O),3366(N-H)cm-1.EI-MS(m/z,%): 451(M+,2).
Compound 13
Gained sterling is yellow solid, yield 87%, m.p.96-98 DEG C.Elementary analysiss/%：Value of calculation：C,51.46;H, 4.77;N,22.11;S,7.23;Measured value：C,51.62;H,4.59;N,22.95;S,6.98;1H NMR(400MHz,DMSO- d6):δ2.30(s,3H,CH3),3.78(s,3H,OCH3),3.81(s,3H,OCH3),5.34(s,2H,CH2),5.45(s,2H, CH2),6.94(s,2H,NH2),7.05(d,1H,J=8.8Hz,Ar-H),7.41(s,1H,Ar-H),7.56(d,1H,J=7.2Hz, Ar-H),8.22(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ25.3,46.7,55.5,55.7,57.6,111.0, 111.6,121.4,123.3,124.9,142.2,148.4,153.1156.0,160.9,161.4,165.2,166.9, 180.3.IR(KBr):1271(C=S),1706(C=O),3365(N-H)cm-1.EI-MS(m/z,%):462(M+,2).
Compound 14
Gained sterling is yellow solid, yield 44%, m.p.>260℃.Elementary analysiss/%：Value of calculation：C,43.13;H, 3.19;N,26.63;S,6.77;Measured value：C,43.35;H,3.42;N,26.12;S,6.53;1H NMR(600MHz,DMSO- d6):δ2.29(s,3H,CH3),5.50(s,2H,CH2),5.52(s,2H,CH2),7.00(s,2H,NH2),8.30(s,1H,CH), 8.87(s,1H,Ar-H),9.03(s,1H,Ar-H).IR(KBr):1277(C=S),1726(C=O),3362(N-H)cm-1.EI- MS(m/z,%):473(M+,4).
Compound 15
Gained sterling is yellow solid, yield 34%, m.p.206-208 DEG C.Elementary analysiss/%：Value of calculation：C,51.46;H, 4.77;N,22.11;S,7.23;Measured value：C,51.27;H,4.49;N,22.22;S,7.38;1H NMR(400MHz,DMSO- d6):δ2.29(s,3H,CH3),3.78(s,3H,OCH3),3.81(s,3H,OCH3),5.34(s,2H,CH2),5.48(s,2H, CH2),6.98(s,2H,NH2),7.04(d,1H,J=8.4Hz,Ar-H),7.41(d,1H,J=1.8Hz,Ar-H),7.56(d,1H, J=8.4Hz,Ar-H).IR(KBr):1271(C=S),1706(C=O),3369(N-H)cm-1.EI-MS(m/z,%):443(M+, 4).
Compound 16
Gained sterling is yellow solid, yield 77%, m.p.141-142 DEG C.Elementary analysiss/%：Value of calculation：C,48.68;H, 3.60;N,23.38;S,7.65;Measured value：C,48.32;H,3.86;N,23.62;S,7.54;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.42(s,2H,CH2),5.59(s,2H,NH2),6.92-7.71(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1265(C=S),1725(C=O),3139(N-H), 3440cm-1.EI-MS(m/z,%):420(M++1,100).
Compound 17
Gained sterling is yellow solid, yield 33%, m.p.230-232 DEG C.Elementary analysiss/%：Value of calculation：C,45.14;H, 3.34;N,21.68;S,7.09;Measured value：C,45.22;H,3.11;N,21.88;S,7.20;1H NMR(400MHz,DMSO- d6):δ2.32(s,3H,CH3),5.39(s,2H,CH2),5.51(s,2H,CH2),7.06(s,2H,NH2),7.53-7.81(m, 3H,Ar-H),8.25(s,1H,CH).IR(KBr):1271(C=S),1712(C=O),3426(N-H)cm-1.EI-MS(m/z,%): 451(M+,2).
Compound 18
Gained sterling is yellow solid, yield 30%, m.p.191-193 DEG C.Elementary analysiss/%：Value of calculation：C,40.09;H, 3.17;N,19.25;S,6.30;Measured value：C,40.20;H,3.45;N,19.18;S,6.16;1H NMR(600MHz,DMSO- d6):δ2.29(s,3H,CH3),4.49(s,2H,CH2),5.43(s,2H,CH2),6.97(s,2H,NH2),7.16-7.85(m, 3H,Ar-H),7.97(s,1H,CH).IR(KBr):1285(C=S),1715(C=O),3364(N-H)cm-1.EI-MS(m/z,%): 509(M+,2).
Compound 19
Gained sterling is yellow solid, yield 40%, m.p.138-140 DEG C.Elementary analysiss/%：Value of calculation：C,47.89;H, 3.57;N,21.72;S,7.10;Measured value：C,47.05;H,3.64;N,21.67;S,7.38;1H NMR(600MHz,DMSO- d6):δ2.30(s,3H,CH3),5.25(s,2H,CH2),5.45(s,2H,CH2),6.95(s,2H,NH2),7.49-7.79(m, 4H,Ar-H),8.01(s,1H,CH),8.03(s,1H,CH).IR(KBr):1323(C=S),1656(C=O),3376(N-H)cm-1.EI-MS(m/z,%):451(M+,2).
Compound 20
Gained sterling is yellow solid, yield 37%, m.p.>260℃.Elementary analysiss/%：Value of calculation：C,52.93;H, 3.95;N,27.43;S,7.85;Measured value：C,52.78;H,3.72;N,27.12;S,7.55;1H NMR(400MHz,DMSO- d6):δ2.50(s,3H,CH3),4.52(s,2H,CH2),5.51(s,2H,CH2),7.11(s,2H,NH2),7.96(m,4H,Ar- H),8.00(s,1H,CH),9.28(s,1H,CH).IR(KBr):1271(C=S),1712(C=O),3426(N-H)cm-1.EI-MS (m/z,%):408(M+,2).
Embodiment 5：Compound 21Preparation
1mmol2- methyl -4- amino -5- azido-methyl pyrimidine and 1mmol propinyl benzoylthioureas are dissolved in 20mL In acetonitrile, add 2mmol diisopropyl ethyl amine and 0.1mmol Hydro-Giene (Water Science)., in 30-40 DEG C of stirring reaction 10-15 hour, TLC（Thin layer chromatography）Monitoring reaction, to complete, add water and has solid to separate out, and through filtration under diminished pressure, washing, dries, obtains crude product.With N, Dinethylformamide and water recrystallization, obtain target compound, are light yellow solid, yield 70%, mp：124-126℃.
Elementary analysiss/%：Value of calculation：C,53.39;H,4.74;N,29.30;S,8.38;Measured value：C,53.04;H, 4.65;N,29.27;S,8.35;1H NMR(400MHz,CDCl3):δ2.49(s,3H,CH3),5.35(s,2H,CH2),5.44 (s,2H,CH2),5.66(s,2H,NH2),7.41-8.03(m,5H,Ar-H),7.72(s,1H,CH),8.19(s,1H,CH).IR (KBr):1265(C=S),1692(C=O),3150(N-H),3410cm-1.EI-MS(m/z,%):383(M++1,100).
Compound 22-40 presses compound 21 similar approach and is obtained, and its Structural Identification data is as follows：
Compound 22
Gained sterling is yellow solid, yield 87%, m.p.115-116 DEG C.Elementary analysiss/%：Value of calculation：C,48.98;H, 4.11;N,26.88;S,7.69;Measured value：C,49.20;H,4.36;N,26.79;S,7.74;1H NMR(400MHz,CDCl3): δ2.50(s,3H,CH3),5.36(s,2H,CH2),5.45(s,2H,CH2),5.58(s,2H,NH2),7.28-7.85(m,4H, Ar-H),7.46(s,1H,CH),8.19(s,1H,CH).IR(KBr):1250(C=S),1717(C=O),3145(N-H), 3544cm-1.EI-MS(m/z,%):417(M++1,100).
Compound 23
Gained sterling is yellow solid, yield 85%, m.p.159-161 DEG C.Elementary analysiss/%：Value of calculation：C,48.98;H, 4.11;N,26.88;S,7.69;Measured value：C,48.99;H,4.43;N,26.52;S,7.39;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.38(s,2H,CH2),5.44(s,2H,CH2),5.66(s,2H,NH2),7.35-7.99(m,4H, Ar-H),7.72(s,1H,CH),8.05(s,1H,CH).IR(KBr):1250(C=S),1722(C=O),3147(N-H), 3454cm-1.EI-MS(m/z,%):417(M++1,100).
Compound 24
Gained sterling is yellow solid, yield 77%, m.p.124-125 DEG C;Elementary analysiss/%：Value of calculation：C,48.98;H, 4.11;N,26.88;S,7.69;Measured value：C,48.92;H,4.54;N,27.11;S,7.50;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.43(s,2H,CH2),5.63(s,2H,NH2),7.39-7.97(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1250(C=S),1708(C=O),3110(N-H), 3452cm-1.EI-MS(m/z,%):417(M++1,100).
Compound 25
Gained sterling is light yellow solid, yield 80%, m.p.156-157 DEG C.Elementary analysiss/%：Value of calculation：C,54.53; H,5.08;N,28.26;S,8.09;Measured value：C,49.68;H,4.85;N,28.40;S,8.14;1H NMR(400MHz, CDCl3):δ2.49(s,3H,CH3),2.62(s,3H,CH3),5.36(s,2H,CH2),5.41(s,2H,CH2),5.67(s,2H, NH2),7.22-7.96(m,4H,Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1702 (C=O),3150(N-H),3512cm-1.EI-MS(m/z,%):397(M++1,100).
Compound 26
Gained sterling is yellow solid, yield 80%, m.p.120-122 DEG C.Elementary analysiss/%：Value of calculation：C,54.53;H, 5.08;N,28.26;S,8.09;Measured value：C,54.31;H,5.11;N,28.17;S,8.22;1H NMR(400MHz,CDCl3): δ2.51(s,3H,CH3),2.65(s,3H,CH3),5.38(s,2H,CH2),5.43(s,2H,CH2),5.54(s,2H,NH2), 7.32-7.93(m,4H,Ar-H),7.71(s,1H,CH),8.08(s,1H,CH).IR(KBr):1270(C=S),1709(C=O), 3118(N-H),3452cm-1.EI-MS(m/z,%):397(M++1,100).
Compound 27
Gained sterling is light yellow solid, yield 90%, m.p.141-143 DEG C.Elementary analysiss/%：Value of calculation：C,50.99; H,4.28;N,27.98;S,8.01;Measured value：C,50.76;H,4.06;N,27.84;S,8.26;1H NMR(400MHz, CDCl3):δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.46(s,2H,CH2),5.60(s,2H,NH2),7.11-7.93 (m,4H,Ar-H),7.52(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1729(C=O),3148(N- H),3453cm-1.EI-MS(m/z,%):401(M++1,100).
Compound 28
Gained sterling is yellow solid, yield 78%, m.p.152-153 DEG C.Elementary analysiss/%：Value of calculation：C,50.99;H, 4.28;N,27.98;S,8.01;Measured value：C,51.03;H,4.01;N,27.84;S,8.26;1H NMR(400MHz,CDCl3): δ2.50(s,3H,CH3),5.36(s,2H,CH2),5.43(s,2H,CH2),5.62(s,2H,NH2),7.10-8.06(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1721(C=O),3111(N-H), 3454cm-1.EI-MS(m/z,%):401(M++1,100).
Compound 29
Gained sterling is yellow solid, yield 86%, m.p.134-136 DEG C.Elementary analysiss/%：Value of calculation：C,44.26;H, 3.71;N,24.29;S,6.95;Measured value：C,44.04;H,3.97;N,24.11;S,6.83;1H NMR(400MHz,CDCl3): δ2.50(s,3H,CH3),5.36(s,2H,CH2),5.45(s,2H,CH2),5.61(s,2H,NH2),7.33-7.80(m,4H, Ar-H),7.66(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1721(C=O),3145(N-H), 3453cm-1.EI-MS(m/z,%):462(M++1,100).
Compound 30
Gained sterling is yellow solid, yield 65%, m.p.165-167 DEG C.Elementary analysiss/%：Value of calculation：C,48.80;H, 3.85;N,26.78;S,7.66;Measured value：C,48.65;H,3.82;N,26.88;S,7.82;1H NMR(400MHz,CDCl3): δ2.49(s,3H,CH3),5.36(s,2H,CH2),5.42(s,2H,CH2),5.59(s,2H,NH2),6.92-7.71(m,4H, Ar-H),7.71(s,1H,CH),8.20(s,1H,CH).IR(KBr):1270(C=S),1725(C=O),3139(N-H), 3440cm-1.EI-MS(m/z,%):419(M++1,100).
Compound 31
Gained sterling is yellow solid, yield 42%, m.p.240-242 DEG C.Elementary analysiss/%：Value of calculation：C,44.21;H, 3.49;N,27.29;S,6.94;Measured value：C,44.55;H,3.67;N,27.46;S,6.62;1H NMR(600MHz,DMSO- d6):δ2.29(s,3H,CH3),4.48(s,2H,J=6.0Hz,CH2),5.48(s,2H,CH2),6.97(s,2H,NH2),7.68 (d,1H,J=8.4Hz,Ar-H),8.02(s,1H,CH),8.21(d,1H,J=8.4Hz,Ar-H),8.32(s,1H,Ar-H), 9.23(s,1H,CH).IR(KBr):1355(C=S),1679(C=O),3218(N-H)cm-1.EI-MS(m/z,%):461(M+, 2).
Compound 32
Gained sterling is yellow solid, yield 50%, m.p.186-188 DEG C.Elementary analysiss/%：Value of calculation：C,45.24;H, 3.57;N,24.83;S,7.10;Measured value：C,45.02;H,3.30;N,24.00;S,7.46;1H NMR(400MHz,DMSO- d6):δ2.29(s,3H,CH3),4.48(s,2H,J=6.0Hz,CH2),5.63(s,2H,CH2),7.08(s,2H,NH2),7.48 (s,2H,Ar-H),7.68(s,1H,Ar-H),8.02(s,1H,Ar-H),8.32(s,1H,Ar-H),9.23(s,1H,CH).IR (KBr):1299(C=S),1666(C=O),3363(N-H)cm-1.EI-MS(m/z,%):450(M+,2).
Compound 33
Gained sterling is yellow solid, yield 62%, m.p.208-209 DEG C.Elementary analysiss/%：Value of calculation：C,51.57;H, 5.01;N,25.32;S,7.25;Measured value：C,51.22;H,5.47;N,25.04;S,7.48;1H NMR(400MHz,DMSO- d6):δ2.30(s,3H,CH3),3.82(s,6H,OCH3),4.47(s,2H,CH2),5.42(s,2H,CH2),6.97(s,2H, NH2),7.04(s,2H,Ar-H),7.60(s,2H,Ar-H),8.02(s,1H,Ar-H),8.32(s,1H,Ar-H),9.12(s, 1H,CH);13C NMR(100MHz,DMSO-d6):δ27.4,34.7,47.2,56.0,113.7,127.1,128.9,130.0, 131.0,132.3,134.4,135.1,138.3,140.6,160.3,161.1,165.3,169.2,192.4.IR(KBr): 1267(C=S),1695(C=O),3334(N-H)cm-1.EI-MS(m/z,%):442(M+,2).
Compound 34
Gained sterling is yellow solid, yield 44%, m.p.181-183 DEG C.Elementary analysiss/%：Value of calculation：C,43.22;H, 3.41;N,29.65;S,6.79;Measured value：C,42.48;H,3.47;N,29.76;S,6.52;1H NMR(400MHz,DMSO- d6):δ2.28(s,3H,CH3),4.57(s,2H,CH2),5.42(s,2H,CH2),6.93(s,2H,NH2),8.07(s,1H,CH), 8.95(s,1H,Ar-H),9.07(s,2H,Ar-H),9.75(s,1H,CH).IR(KBr):1344(C=S),1672(C=O), 3414(N-H)cm-1.EI-MS(m/z,%):472(M+,2).
Compound 35
Gained sterling is yellow solid, yield 34%, m.p.191-193 DEG C.Elementary analysiss/%：Value of calculation：C,51.57;H, 5.01;N,25.32;S,7.25;Measured value：C,50.60;H,5.42;N,25.17;S,7.05;1H NMR(400MHz,DMSO- d6):δ2.32(s,3H,CH3),3.75(s,3H,OCH3),3.78(s,3H,OCH3),4.85(s,2H,CH2),5.48(s,2H, CH2),6.97(s,2H,NH2),6.67-7.34(m,3H,Ar-H),8.13(s,1H,CH),11.00(s,1H,NH),11.76(s, 1H,NH).IR(KBr):1288(C=S),1631(C=O),3432(N-H)cm-1.EI-MS(m/z,%):442(M+,5).
Compound 36
Gained sterling is yellow solid, yield 97%, m.p.228-230 DEG C.Elementary analysiss/%：Value of calculation：C,48.80;H, 3.85;N,26.78;S,7.66;Measured value：C,48.63;H,3.73;N,26.13;S,7.48;1H NMR(400MHz,DMSO- d6):δ2.30(s,3H,CH3),4.48(d,2H,J=5.2Hz,CH2),5.43(s,2H,CH2),6.94(s,2H,NH2),7.14- 7.71(m,3H,Ar-H),8.00(s,1H,CH),8.83(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ25.2, 46.6,67.0,104.2,104.5,104.8,111.6,111.8,120.2,120.4,123.0,131.8,131.9,144.8, 158.5,158.6,161.0,161.1,161.4,162.1,162.2,162.8,164.7.IR(KBr):1432(C=S),1663 (C=O),3309(N-H)cm-1.EI-MS(m/z,%):442(M+,5).
Compound 37
Gained sterling is yellow solid, yield 45%, m.p.164-166 DEG C.Elementary analysiss/%：Value of calculation：C,45.24;H, 3.57;N,24.83;S,7.10;Measured value：C,45.60;H,3.44;N,24.13;S,7.36;1H NMR(400MHz,DMSO- d6):δ2.32(s,3H,CH3),4.39(s,2H,CH2),5.51(s,2H,CH2),7.06(s,2H,NH2),7.53-7.81(m, 3H,Ar-H),8.25(s,1H,CH).IR(KBr):1431(C=S),1644(C=O),3428(N-H)cm-1.EI-MS(m/z,%): 450(M+,2).
Compound 38
Gained sterling is yellow solid, and yield is 30%, m.p.206-208 DEG C.Elementary analysiss/%：Value of calculation：C,40.17; H,3.37;N,22.04;S,6.31;Measured value：C,40.32;H,3.55;N,22.77;S,6.19;1H NMR(400MHz, DMSO-d6):δ2.30(s,3H,CH3),4.43(s,2H,CH2),5.44(s,2H,CH2),6.98(s,2H,NH2),7.16-7.85 (m,4H,Ar-H),8.00(s,1H,CH),8.91(s,1H,CH).IR(KBr):1389(C=S),1664(C=O),3335(N-H) cm-1.EI-MS(m/z,%):508(M+,2).
Compound 39
Gained sterling is yellow solid, yield 40%, m.p.230-232 DEG C.Elementary analysiss/%：Value of calculation：C,48.00;H, 3.80;N,24.88;S,7.12;Measured value：C,48.18;H,3.95;N,24.44;S,7.55;1H NMR(400MHz,DMSO- d6):δ2.29(s,3H,CH3),4.52(s,2H,CH2),5.39(s,2H,CH2),6.91(s,2H,NH2),7.85(s,2H,Ar- H),8.02(s,2H,Ar-H),8.04(s,1H,CH),9.26(s,1H,CH).IR(KBr):1336(C=S),1631(C=O), 3423(N-H)cm-1.EI-MS(m/z,%):450(M+,2).
Compound 40
Gained sterling is yellow solid, yield 35%, m.p.193-195 DEG C.Elementary analysiss/%：Value of calculation：C,53.06;H, 4.21;N,30.94;S,7.87;Measured value：C,53.14;H,4.06;N,30.01;S,7.65;1H NMR(400MHz,DMSO- d6):δ2.40(s,3H,CH3),4.51(s,2H,CH2),5.46(s,2H,CH2),7.02(s,2H,NH2),7.99(m,4H,Ar- H),7.99(s,2H,Ar-H),9.28(s,1H,CH).IR(KBr):1285(C=S),1663(C=O),3416(N-H)cm-1.EI- MS(m/z,%):407(M+,2).
Embodiment 6：Compound 41Preparation
2.0mmol2- methyl -4- amino -5- azido-methyl pyrimidine, 2.0mmol tri- second is added in 50mL round-bottomed flask Amine, 10mL anhydrous acetonitrile, 2.1mmol5- phenyl-（1,3,4- thiadiazoles）- 2- sulfenyl propine, stirring and dissolving, add The CuI of 0.1mmol, stirring reaction under room temperature, TLC（Thin layer chromatography）To complete, the stirring that adds water has solid to separate out, and takes out for monitoring reaction Filter, washing, the crude product of drying, through ethyl alcohol recrystallization, obtain target compound, are white solid, yield 91%, mp：121-123℃.
1H NMR(600MHz,DMSO-d6)δ(ppm):2.32(s,3H,CH3),4.65(s,2H,-SCH2-),5.44(s, 2H,CH2),7.04(s,2H,NH2),7.58-7.97(m,5H,H-Ph),8.16(s,1H,pyrimidin-5-yl-H);IR (KBr):ν3385(N-H),3140,2361,2356,1663,1594,1574,1471,1430,1224,1195,1120,1064, 995,837,814,780,706;HRMS(calcd.)[M+Na]+:419.0837(419.0740).
Compound 42-74 presses compound 41 similar approach and is obtained, and its Structural Identification data is as follows：
Compound 42
Gained sterling is yellow solid, yield 90%, m.p.128-130 DEG C;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.29(s,3H,CH3),4.63(s,2H,-SCH2-),5.42(s,2H,CH2),6.93(s,2H,NH2),7.57-8.25(m,4H, 1H,H3,5and6-Ph,pyrimidin-5-yl-H);IR(KBr):3337(N-H),3196,2369,2359,2100,1600, 1564(N=O),1466,1345(N=O),1260,1228,1194,1121,1089,1048,855,807,725.
Compound 43
Gained sterling is yellow solid, yield 91%;m.p.137-139℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.28(s,3H,CH3),4.66(s,2H,-SCH2-),5.41(s,2H,CH2),6.91(s,2H,NH2),8.14(s,1H, pyrimidin-5-yl-H),8.20-8.43(m,4H,H2,3,5and6-Ph);IR(KBr):3400(N-H),3142,2363, 2354,1632,1595,1558,1521(N=O),1463,1346(N=O),1190,1115,1069,855,808,790,708; HRMS(calcd.)[M+Na]+:464.0688(464.0695).
Compound 44
Gained sterling is white solid, yield 91%;m.p.157-160℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.29(s,3H,CH3),4.63(s,2H,-SCH2-),5.43(s,2H,CH2),6.97(s,2H,NH2),7.55-7.95(m,4H, H3,4,5and6-Ph),8.14(s,1H,pyrimidin-5-yl-H);IR(KBr):3379(N-H),3140,2364,2355, 1660,1595,1572,1478,1431,1196,1120,1091,1050,814,779,762,729;HRMS(calcd.)[M+ Na]+:453.0447(453.0393).
Compound 45
Gained sterling is white solid, yield 91%;m.p.169-171℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.30(s,3H,CH3),4.62(s,2H,-SCH2-),5.42(s,2H,CH2),6.93(s,2H,NH2),6.93-7.40(m,4H, H2,3,5and6-Ph),8.13(s,1H,pyrimidin-5-yl-H);IR(KBr):3334(N-H),3162,2364,2359, 1664,1593,1571,1472,1426,1222,1197,1118,1094,1068,1054,839,813,782,729.
Compound 46
Gained sterling is yellow solid, yield 92%;m.p.117-120℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.29(s,3H,CH3),4.63(s,2H,-SCH2-),5.42(s,2H,CH2),6.93(s,2H,NH2),7.93-8.19(m,4H, 1H,H3,4,5and6-Ph,pyrimidin-5-yl-H);IR(KBr):3411(N-H),3144,2453,2353,1662,1647, 1596,1572,1528(N=O),1465,1432,1352(N=O),1196,1118,1065,996,857,809,789,726; HRMS(calcd.)[M+Na]+:464.0688(464.0676).
Compound 47
Gained sterling is white solid, yield 93%;m.p.133-135℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.29(s,3H,CH3),4.63(s,2H,-SCH2-),5.42(s,2H,CH2),6.93(s,2H,NH2),7.07-7.63(m,3H, H3,5and6-Ph),8.13(s,1H,pyrimidin-5-yl-H);IR(KBr):3327(N-H),3167,2394,2354,1658, 1593,1568,1474,1426,1373,1194,1148,1118,1089,1051,864,813,777,731.
Compound 48
Gained sterling is white solid, yield 93%;m.p.137-139℃;1H NMR(600MHz,DMSO-d6)δ(ppm): 2.29(s,3H,CH3),4.61(s,2H,-SCH2-),5.43(s,2H,CH2),6.96(s,2H,NH2),7.41-7.44(m,2H, H2,6-Ph),7.99-8.00(m,2H,H3,5-Ph),8.13(s,1H,pyrimidin-5-yl-H);IR(KBr):3334(N-H), 3150,2432,2354,1665,1609,1594,1573,1501,1473,1426,1357,1228,1192,1119,1066, 845,814,781,732;HRMS(calcd.)[M+Na]+:437.0743(437.0713).
Compound 49
Gained sterling is white solid, yield 91%;m.p.115-117℃;1H NMR(600MHz,DMSO-d6)δ(ppm): 2.28(s,3H,CH3),4.65(s,2H,-SCH2-),5.41(s,2H,CH2),6.94(s,2H,NH2),7.96-7.98(m,2H, H2,6-Ph),8.13-8.15(m,3H,H3,5-Ph,pyrimidin-5-yl-H);IR(KBr):3389(N-H),3069,2400, 2354,1664,1595,1558,1505,1468,1416,1324,1197,1166,1111,1077,1058,857,812,791; HRMS(calcd.)[M+Na]+:487.0711(487.0722).
Compound 50
Gained sterling is yellow solid, yield 85%;m.p.144-147℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.30(s,3H,CH3),4.65(s,2H,-SCH2-),5.43(s,2H,CH2),6.91(s,2H,NH2),7.55-7.78(m,3H, H2,4and6-Ph),8.15(s,1H,pyrimidin-5-yl-H);IR(KBr):3364(N-H),3222,2363,2354,1633, 1598,1561,1531(N=O),1470,1346,(N=O)1283,1235,1180,1102,991,865,811,750,720.
Compound 51
Gained sterling is yellow solid, yield 88%;m.p.151-153℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.28(s,3H,CH3),4.67(s,2H,-SCH2-),5.42(s,2H,CH2),6.94(s,2H,NH2),7.87(s,1H,H1- Ph),8.15(s,1H,pyrimidin-5-yl-H),8.35-8.63(m,3H,H4,5and6-Ph);IR(KBr):3370(N-H), 2355,2335,1629,1597,1557,1528(N=O),1462,1433,1352(N=O),1229,1198,1113,1058, 972,871,811,789,744,709;HRMS(calcd.)[M+Na]+:464.0688(464.0638).
Compound 52
Gained sterling is white solid, yield 90%;m.p.139-141℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.63(s,2H,-SCH2-),5.48(s,2H,CH2),7.02(s,2H,NH2),7.40-7.99(m,4H, H3,4,5and6-Ph),8.15(s,1H,pyrimidin-5-yl-H);IR(KBr):3401(N-H),3132,2440,2356, 1666,1600,1564,1493,1477,1437,1337,1222,1183,1118,1054,814,790,771,736;HRMS (calcd.)[M+Na]+:437.0743(437.0700).
Compound 53
Gained sterling is yellow solid, and yield is 70%;m.p.170-171℃;Elementary analysiss/%：Value of calculation：C,42.95; H,3.18;N,23.57;S,13.49;Measured value：C,43.36;H,3.39;N,23.21;S,13.14;1HNMR(400MHz, DMSO-d6(ppm):2.28(s,3H,CH3),4.62(s,2H,-SCH2-),5.41(s,2H,CH2),6.91(s,2H,NH2), 7.54-7.58(m,2H,H-Ph),7.84-7.89(m,2H,H-Ph),8.02(s,1H,1,2,3-triazol-4-yl-H); 8.14(s,1H,pyrimidin-5-yl-H),13CNMR(100MHz,DMSO-d6)δ(ppm):25.4,26.9,47.0,109.7, 120.9,124.4,128.5,131.8,133.6,134.6,142.6,148.1,156.3,161.6,164.3.
Compound 54
Gained sterling is light yellow solid, yield 52%;m.p.180-182℃;Elementary analysiss/%：Value of calculation：C,50.69; H,4.25;N,26.27;S,15.04;Measured value：C,50.42;H,4.46;N,26.24;S,15.15;1H NMR(400MHz, DMSO-d6)δ(ppm):2.29(s,3H,CH3),3.84(s,3H,OCH3),4.61(s,2H,-SCH2-),5.42(s,2H, CH2),6.94(s,2H,NH2),7.13(d,2H,J=10.8Hz,Ar-H),7.89(d,2H,J=10.8Hz,Ar-H),8.14(s, 1H,pyrimidin-5-yl-H).
Compound 55
Gained sterling is light yellow solid, yield 71%;m.p.209-211℃;Elementary analysiss/%：Value of calculation：C,52.66; H,4.42;N,27.30;S,15.62;Measured value：C,52.68;H,4.49;N,27.27;S,15.48;1H NMR(400MHz, DMSO-d6)δ(ppm):2.28(s,3H,CH3),2.38(s,3H,CH3),4.61(s,2H,-SCH2-),5.40(s,2H,CH2), 6.93(s,2H,NH2),7.39(d,2H,J=8.0Hz,Ar-H),7.84(d,2H,J=8.0Hz,Ar-H),7.98(s,1H,1,2, 3-triazol-4-yl-H),8.14(s,1H,pyrimidin-5-yl-H).
Compound 56
Gained sterling is brown solid, yield 62%;m.p.155-156℃;Elementary analysiss/%：Value of calculation：C,52.66;H, 4.42;N,27.30;S,15.62;Measured value：C,51.90;H,4.85;N,26.66;S,15.39;1H NMR(600MHz, DMSO-d6)δ(ppm):2.39(s,3H,CH3),2.61(s,3H,CH3),4.75(s,2H,-SCH2-),5.52(s,2H,CH2), 7.05(s,2H,NH2),7.55-7.59(m,2H,Ar-H),7.86-7.90(m,2H,Ar-H),8.08(s,1H,1,2,3- triazol-4-yl-H),8.25(s,1H,pyrimidin-5-yl-H).
Compound 57
Gained sterling is light yellow solid, yield 74%;m.p.149-151℃;1H NMR(600MHz,DMSO-d6)δ (ppm):2.29(s,3H,CH3),2.57(s,3H,CH3),4.64(s,2H,-SCH2-),5.42(s,2H,CH2),6.95(s, 2H,NH2),7.41(d,2H,J=27.0Hz,H-Ph),7.49(d,H,H-Ph),7.85(d,2H,J=7.2Hz,Ar-H),7.90 (s,1H,1,2,3-triazol-4-yl-H),8.06(s,1H,pyrimidin-5-yl-H).
Compound 58
Gained sterling is yellow solid, yield 93%;m.p.162-164℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.32(s,3H,CH3),4.64(s,2H,-SCH2-),5.42(s,2H,CH2),7.00(s,2H,NH2),7.52-7.99(m,3H, H3,5and6-Ph),8.13(s,1H,pyrimidin-5-yl-H);IR(KBr):3356(N-H),3132,2355,2332,2097, 1629,1594,1559(N=O),1467,1345(N=O),1260,1227,1193,1089,1050,883,806,729.
Compound 59
Gained sterling is yellow solid, yield 90%;m.p.143-145℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.63(s,2H,-SCH2-),5.44(s,2H,CH2),6.97(s,2H,NH2),7.91-8.18(m,4H, 1H,H3,4,5and6-Ph,pyrimidin-5-yl-H);13C NMR(100MHz,DMSO-d6)δ(ppm):25.11,26.86, 46.78,108.35,123.92,124.56,127.74,128.48,142.25,149.15,155.89,161.45,163.98, 164.51,167.18;HRMS(calcd.)[M+H]+:426.1097(426.1102).
Compound 60
Gained sterling is yellow solid, yield 86%;m.p.126-128℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.63(s,2H,-SCH2-),5.44(s,2H,CH2),6.97(s,2H,NH2),7.08-7.41(m,4H, H3,4,5and6-Ph),8.11(s,1H,pyrimidin-5-yl-H);IR(KBr):3382(N-H),3141,2355,2334, 1660,1595,1572,1468,1431,1359,1196,1120,1091,1071,1051,998,863,815,779,763, 729;HRMS(calcd.)[M+H]+:415.0856(415.0831).
Compound 61
Gained sterling is white solid, yield 93%;m.p.189-191℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.63(s,2H,-SCH2-),5.44(s,2H,CH2),6.97(s,2H,NH2),6.93-7.40(m,4H, H2,3,5and6-Ph),8.13(s,1H,pyrimidin-5-yl-H);IR(KBr):3337(N-H),3157,2462,2357, 1664,1591,1570,1475,1426,1406,1222,1197,1117,1095,1068,1053,1012,839,813,782, 729;HRMS(calcd.)[M+H]+:415.0856(415.0890).
Compound 62
Gained sterling is yellow solid, yield 90%;m.p.171-173℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.63(s,2H,-SCH2-),5.44(s,2H,CH2),6.97(s,2H,NH2),7.91-8.18(m,4H, 1H,H3,4,5and6-Ph,pyrimidin-5-yl-H);IR(KBr):3415(N-H),3145,2353,1648,1597,1569, 1527(N=O),1465,1431,1352(N=O),1195,1118,1065,986,857,808,751,725;HRMS(calcd.) [M+H]+:426.1097(426.1082).
Compound 63
Obtaining sterling is white solid, yield 91%;m.p.173-175℃;1H NMR(600MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.64(s,2H,-SCH2-),5.45(s,2H,CH2),7.00(s,2H,NH2),7.63-7.97(m,3H, H3,5and6-Ph),8.15(s,1H,pyrimidin-5-yl-H);IR(KBr):3336(N-H),3174,2418,2360,1657, 1594,1568,1475,1430,1217,1195,1119,1090,1052,1037,865,832,814,778,732;HRMS (calcd.)[M+Na]+:471.0286(471.0320).
Compound 64
Gained sterling is white solid, yield 89%;132-134℃;1H NMR(600MHz,DMSO-d6)δ(ppm):2.31 (s,3H,CH3),4.63(s,2H,-SCH2-),5.43(s,2H,CH2),7.01(s,2H,NH2),7.40-7.44(m,2H,H2,6- Ph),7.99-8.01(m,2H,H3,5-Ph),8.15(s,1H,pyrimidin-5-yl-H);IR(KBr):3428(N-H), 3152,2360,2357,1665,1595,1574,1502,1474,1426,1228,1192,1158,1121,1067,997, 956,846,815,782,733;HRMS(calcd.)[M+H]+:399.1152(399.1151).
Compound 65
Gained sterling is white solid, yield 89%;132-134℃;1H NMR(600MHz,DMSO-d6)δ(ppm):2.29 (s,3H,CH3),4.66(s,2H,-SCH2-),5.42(s,2H,CH2),6.98(s,2H,NH2),7.96-7.97(m,2H,H2,6- Ph),8.14-8.16(m,3H,H3,5-Ph,pyrimidin-5-yl-H);IR(KBr):3423(N-H),3069,2360,2357, 1665,1595,1559,1508,1468,1416,1325,1198,1167,1110,1077,1058,1015,857,812,792; HRMS(calcd.)[M+H]+:449.1120(449.1133).
Compound 66
Gained sterling is white solid, yield 88%;m.p.138-140℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.37(s,3H,CH3),4.66(s,2H,-SCH2-),5.47(s,2H,CH2),7.10(s,2H,NH2),7.58-7.95(m,5H, H-Ph),8.18(s,1H,pyrimidin-5-yl-H);HRMS(calcd.)[M+H]+:381.1246(381.1236).
Compound 67
Gained sterling is yellow solid, yield 87%;m.p.163-165℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.65(s,2H,-SCH2-),5.43(s,2H,CH2),6.97(s,2H,NH2),7.52-7.75(m,3H, H2,4and6-Ph),8.14(s,1H,pyrimidin-5-yl-H);IR(KBr):3369(N-H),3230,2366,2359,1640, 1595,1567,1544(N=O),1472,1351(N=O),1279,1231,1180,1102,990,868,811,750,723.
Compound 68
Gained sterling is yellow solid, yield 90%;m.p.171-173℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.28(s,3H,CH3),4.66(s,2H,-SCH2-),5.43(s,2H,CH2),6.91(s,2H,NH2),7.89(s,1H,H1- Ph),8.14(s,1H,pyrimidin-5-yl-H),8.41-8.65(m,3H,H4,5and6-Ph);IR(KBr):3399(N-H), 3132,2362,2355,1660,1593,1562,1527(N=O),1471,1353(N=O),1233,1123,1063,994, 868,813,742,710;HRMS(calcd.)[M+H]+:426.1097(426.1069).
Compound 69
Gained sterling is white solid, yield 90%;m.p.165-168℃;1H NMR(400MHz,DMSO-d6)δ(ppm): 2.31(s,3H,CH3),4.62(s,2H,-SCH2-),5.43(s,2H,CH2),7.08(s,2H,NH2),7.41-7.97(m,4H, H3,4,5and6-Ph),8.13(s,1H,pyrimidin-5-yl-H);IR(KBr):3401(N-H),3133,2440,1665, 1619,1598,1565,1494,1476,1438,1338,1223,1185,1119,1054,994,959,813,790,770, 737;HRMS(calcd.)[M+H]+:399.1152(399.1143).
Compound 70
Gained sterling is brown solid, yield 72%;m.p.167-168℃;1H NMR(400MHz,DMSO-d6)δ (ppm):2.29(s,3H,CH3),4.64(s,2H,-SCH2-),5.42(s,2H,CH2),6.94(s,2H,NH2),7.56(s, 2H,H-Ph),7.88(s,2H,H-Ph),8.01(s,1H,1,2,3-triazol-4-yl-H),8.15(s,1H,pyrimidin- 5-yl-H).
Compound 71
Gained sterling is light yellow solid, yield 88%;m.p.180-181℃;Elementary analysiss/%：Value of calculation：C,52.67; H,4.42;N,27.30;O,7.80;S,7.81;Measured value：C,52.38;H,4.16;N,27.63;S,7.83;1H NMR (600MHz,DMSO-d6)δ(ppm):2.28(s,3H,CH3),3.84(s,3H,OCH3),4.60(s,2H,-SCH2-),5.40 (s,2H,CH2),6.93(s,2H,NH2),7.11(d,2H,J=12Hz,Ar-H),7.88(d,2H,J=12Hz,Ar-H),7.98 (s,1H,1,2,3-triazol-4-yl-H),8.15(s,1H,pyrimidin-5-yl-H).
Compound 72
Gained sterling is light yellow solid, yield 79%;m.p.215-217℃;1H NMR(400MHz,DMSO-d6)δ (ppm):2.40(s,3H,CH3),2.61(s,3H,CH3),4.73(s,2H,-SCH2-),5.52(s,2H,CH2),7.04(s, 2H,NH2),7.52(s,2H,H-Ph),7.95(d,2H,J=5.6Hz,Ar-H),8.08(s,1H,1,2,3-triazol-4-yl- H),8.27(s,1H,pyrimidin-5-yl-H).
Compound 73
Gained sterling is brown solid, yield 85%;m.p.152-153℃;Elementary analysiss/%：Value of calculation：C,54.81;H, 4.60;N,28.41;S,8.13;Measured value：C,54.59;H,4.85;N,27.94;S,8.20;1H NMR(600MHz,DMSO- d6)δ(ppm):2.40(s,3H,CH3),2.62(s,3H,CH3),4.75(s,2H,-SCH2-),5.52(s,2H,CH2),7.05 (s,2H,NH2),7.56-7.60(m,2H,Ar-H),7.87-7.91(m,2H,Ar-H),8.07(s,1H,1,2,3-triazol- 4-yl-H),8.25(s,1H,pyrimidin-5-yl-H).
Compound 74
Gained sterling is brown solid, yield 65%;m.p.152-153℃;Elementary analysiss/%：Value of calculation：C,54.81;H, 4.60;N,28.41;S,8.13;Measured value：C,54.89;H,4.38;N,28.86;S,7.85;1H NMR(600MHz,DMSO- d6)δ(ppm):2.29(s,3H,CH3),2.58(s,3H,CH3),4.63(s,2H,-SCH2-),5.41(s,2H,CH2),6.94 (s,2H,NH2),7.39-7.50(m,3H,H-Ph),7.85(d,H,J=8.4Hz,Ar-H),7.96(s,1H,1,2,3- triazol-4-yl-H),8.14(s,1H,pyrimidin-5-yl-H).
Embodiment 7：Compound 75Preparation
1mmol2- methyl -4- amino -5- azido-methyl pyrimidine, 1mmol O- is sequentially added propargyl in 100mL round-bottomed flask Base -4- fluorophenethyl ketoxime ether, 2mmol triethylamine, are dissolved in 10mL anhydrous tetrahydro furan（THF）, stir under room temperature, treat solid dissolving Afterwards, add 0.1mmol Hydro-Giene (Water Science)., under room temperature, react 10-15 hour, TLC（Thin layer chromatography）React to complete, the stirring that adds water has Solid separates out, decompression sucking filtration, washing, the crude product dried, and uses dimethylformamide（DMF）With water recrystallization, obtain yellow solid, produce Rate 71%, mp：96-97℃.
Elementary analysiss/%：Value of calculation：C,57.46;H,5.11;N,27.59;Measured value：C,57.65;H,5.18;N, 27.26;1HNMR(600MHz,DMSO-d6):δ2.14(s,3H,CH3),2.29(s,3H,CH3),5.20(s,2H,CH2),5.44 (s,2H,CH2),6.95(s,2H,NH2),7.23(d,2H,J=8.4Hz,Ar-H),7.67(s,2H,J=6.0Hz,Ar-H),8.01 (s,1H,CH),8.18(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ12.5,25.2,46.7,66.9,108.4, 115.2,115.8,124.6,128.1,128.2,132.3,143.5,153.9,156.2,161.5,164.0,167.2.IR (KBr):1663(C=N),3431(N-H)cm-1.EI-MS(m/z,%):355(M+,11).
Compound 76-95 presses compound 75 similar approach and is obtained, and its Structural Identification data is as follows：
Compound 76
Gained sterling is yellow solid, yield 66%, m.p.180-183 DEG C;Elementary analysiss/%：Value of calculation：C,49.05;H, 4.36;N,23.55;Measured value：C,49.23;H,4.54;N,23.91;1H NMR(600MHz,DMSO-d6):δ2.13(s,3H, CH3),2.29(s,3H,CH3),5.20(s,2H,CH2),5.49(s,2H,CH2),7.02(s,2H,NH2),7.56-7.61(m, 4H,Ar-H),8.19(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ12.5,25.5,46.7,66.9,111.0, 122.6,124.6,127.8,130.0,131.3,134.8,143.5,155.7,161.3,168.7.IR(KBr):1674(C= N),3296(N-H)cm-1.EI-MS(m/z,%):415(M+,7).
Compound 77
Gained sterling is yellow solid, yield 90%, m.p.184-186 DEG C;Elementary analysiss/%：Value of calculation：C,54.91;H, 4.88;N,26.37;Measured value：C,54.45;H,4.75;N,26.18;1H NMR(600MHz,DMSO-d6):δ2.14(s,3H, CH3),2.30(s,3H,CH3),5.20(s,2H,CH2),5.44(s,2H,CH2),6.98(s,2H,NH2),7.47(s,2H,Ar- H),7.64(s,2H,Ar-H),8.19(s,1H,CH);13C NMR(100MHz,DMSO-d6):δ12.5,25.5,46.7,66.9, 111.0,122.6,124.6,127.8,130.0,131.3,134.8,143.5,155.7,161.3,168.7.IR(KBr): 1676(C=N),3299(N-H)cm-1.EI-MS(m/z,%):371(M+,7).
Compound 78
Gained sterling is yellow solid, yield 73%, m.p.131-132 DEG C;Elementary analysiss/%：Value of calculation：C,60.52;H, 5.68;N,29.06;Measured value：C,59.85;H,5.65;N,29.35;1H NMR(600MHz,DMSO-d6):δ2.15(s,3H, CH3),2.29(s,3H,CH3),5.20(s,2H,CH2),5.44(s,2H,CH2),6.98(s,2H,NH2),7.40(d,2H,J= 2.4Hz,Ar-H),7.63(d,2H,J=3.0Hz,Ar-H),8.01(s,1H,Ar-H),8.19(s,1H,CH);13C NMR (100MHz,DMSO-d6):δ12.5,25.2,46.7,66.8,108.3,124.6,125.9,128.4,129.2,135.8, 143.5,154.7,156.2,161.5,167.0.IR(KBr):1664(C=N),3327(N-H)cm-1.EI-MS(m/z,%):337 (M+,8).
Compound 79
Gained sterling is yellow solid, yield 64%, m.p.154-156 DEG C;Elementary analysiss/%：Value of calculation：C,58.84;H, 5.76;N,26.69;Measured value：C,58.58;H,5.62;N,26.13;1H NMR(600MHz,DMSO-d6):δ2.12(s,3H, CH3),2.29(s,3H,CH3),3.37(s,3H,OCH3),5.16(s,2H,CH2),5.43(s,2H,CH2),6.94(s,2H, NH2),6.96(s,2H,Ar-H),7.58(d,2H,J=3.0Hz,Ar-H),8.17(s,1H,Ar-H);13C NMR(100MHz, DMSO-d6):δ12.4,25.2,46.6,55.1,66.7,108.4,113.8,124.5,127.3,128.2,143.6,156.2, 160.1,161.5,167.0,183.0.IR(KBr):1669(C=N),3323(N-H)cm-1.EI-MS(m/z,%):367(M+, 10).
Compound 80
Gained sterling is yellow solid, yield 66%, m.p.222-224 DEG C;Elementary analysiss/%:Value of calculation：C,53.40;H, 4.74;N,29.30;Measured value：C,53.61;H,4.31;N,29.12;1H NMR(600MHz,DMSO-d6):δ2.21(s,3H, CH3),2.30(s,3H,CH3),5.27(s,2H,CH2),5.47(s,2H,CH2),6.98(s,2H,NH),7.89(s,2H,Ar- H),8.21(s,1H,CH),8.25(d,2H,J=7.2Hz,Ar-H);IR(KBr):1673(C=N),3302(N-H)cm-1.
Compound 81
Gained sterling is yellow solid, yield 50%, m.p.126-127 DEG C;Elementary analysiss/%：Value of calculation：C,57.46;H, 5.11;N,27.59;Measured value：C,57.15;H,5.12;N,27.32;1H NMR(600MHz,DMSO-d6):δ2.13(s,3H, CH3),2.30(s,3H,CH3),5.20(s,2H,CH2),5.45(s,2H,CH2),6.98(s,2H,NH),7.22-7.46(s, 4H,Ar-H),8.04(s,1H,CH),8.17(s,1H,CH);IR(KBr):1639(C=N),3384(N-H)cm-1.
Compound 82
Gained sterling is yellow solid, yield 67%, m.p.188-190 DEG C;Elementary analysiss/%：Value of calculation：C,54.91;H, 4.88;N,26.37;Measured value：54.18;H,4.72;N,26.46;1H NMR(600MHz,DMSO-d6):δ2.14(s,3H, CH3),2.29(s,3H,CH3),5.20(s,2H,CH2),5.45(s,2H,CH2),6.98(s,2H,NH),7.46(s,2H,Ar- H),7.64(s,2H,Ar-H),8.19(s,1H,CH);IR(KBr):1676(C=N),3297(N-H)cm-1.
Compound 83
Gained sterling is yellow solid, yield 64%, m.p.131-133 DEG C;Elementary analysiss/%：Value of calculation：C,54.91;H, 4.88;N,26.37;Measured value：C,54.48;H,4.62;N,26.26;1H NMR(600MHz,DMSO-d6):δ2.15(s,3H, CH3),2.29(s,3H,CH3),5.22(s,2H,CH2),5.44(s,2H,CH2),6.95(s,2H,NH),7.42-7.48(m, 2H,Ar-H),7.60(d,1H,J=7.2Hz,Ar-H),7.67(s,1H,Ar-H),8.00(s,1H,CH),8.19(s,1H,CH); IR(KBr):1670(C=N),3389(N-H)cm-1.
Compound 84
Gained sterling is yellow solid, yield 34%, m.p.109-110 DEG C;Elementary analysiss/%：Value of calculation：C,53.40;H, 4.74;N,29.30;Measured value：C,53.11;H,4.69;N,29.57;1H NMR(600MHz,DMSO-d6):δ2.10(s,3H, CH3),2.30(s,3H,CH3),5.12(s,2H,CH2),5.43(s,2H,CH2),6.95(s,2H,NH),7.56(d,1H,J= 7.8Hz,Ar-H),7.67(t,1H,J=7.2Hz,Ar-H),7.78(t,1H,J=7.2Hz,Ar-H),8.00(s,1H,CH), 8.02(d,1H,J=8.4Hz,Ar-H),8.11(s,1H,CH);IR(KBr):1669(C=N),3385(N-H)cm-1.
Compound 85
The sterling of gained is white solid, yield 74%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.10(s,3H, CH3),2.32(s,3H,CH3),5.19(s,2H,CH2),5.46(s,2H,CH2),7.00(s,2H,NH2),7.34(s,1H,Ar- H),7.50(s,1H,Ar-H),7.70(s,1H,Ar-H).IR(KBr)υ(cm-1):3414(NH2),2972(CH3),1667(C= N),1646-1227(Ar).
Compound 86
Gained sterling is yellow solid, yield 70%, m.p.190-192 DEG C;Elementary analysiss/%：Value of calculation：C,48.99;H, 3.85;N,25.00;Measured value：C,48.29;H,3.88;N,25.12;1H NMR(600MHz,DMSO-d6):δ2.30(s,3H, CH3),5.25(s,2H,CH2),5.45(s,2H,CH2),6.95(s,2H,NH),7.49-7.79(m,3H,Ar-H),8.01(s, 1H,CH),8.22(s,1H,CH),8.39(s,1H,CH);IR(KBr):1676(C=N),3346(N-H)cm-1.
Compound 87
Gained sterling is yellow solid, yield 78%, m.p.185-187 DEG C;Elementary analysiss/%：Value of calculation：C,53.71;H, 4.51;N,27.40;Measured value：C,53.32;H,4.56;N,27.02;1H NMR(600MHz,DMSO-d6):δ2.28(s,3H, CH3),5.18(s,2H,CH2),5.43(s,2H,CH2),6.94(s,2H,NH),7.48(d,2H,J=8.4Hz,Ar-H),7.61 (d,2H,J=8.4Hz,Ar-H),7.94(s,2H,CH),8.19(s,1H,CH),8.25(s,1H,CH).
Compound 88
Gained sterling is yellow solid, yield 86%, m.p.179-181 DEG C;Elementary analysiss/%：Value of calculation：C,47.44;H, 4.01;N,24.37;Measured value：C,46.95;H,4.10;N,24.21;1H NMR(600MHz,DMSO-d6):δ2.31(s,3H, CH3),3.78(s,3H,CH3),5.15(s,2H,CH2),5.47(s,2H,CH2),6.98(s,2H,NH),6.98(s,4H,Ar- H),7.62(d,2H,J=7.8Hz,Ar-H),7.94(s,1H,CH),8.19(s,1H,CH),8.24(s,1H,CH).
Compound 89
Gained sterling is yellow solid, yield 74%, m.p.168-170 DEG C;Elementary analysiss/%：Value of calculation：C,56.30;H, 4.72;N,28.72;Measured value：C,56.49;H,4.38;N,28.52;1H NMR(600MHz,DMSO-d6):δ2.30(s,3H, CH3),5.18(s,2H,CH2),5.46(s,2H,CH2),6.99(s,2H,NH),7.26(s,2H,Ar-H),7.94(s,1H, CH),8.19(s,1H,CH),8.25(s,1H,CH).
Compound 90
Gained sterling is yellow solid, yield 30%, m.p.100-101 DEG C;Elementary analysiss/%：Value of calculation：C,57.78;H, 5.42;N,27.75;Measured value：C,57.30;H,5.41;N,27.56;1H NMR(600MHz,DMSO-d6):δ2.31(s,3H, CH3),3.78(s,3H,OCH3),5.15(s,2H,CH2),5.47(s,2H,CH2),6.98(s,4H,Ar+NH),7.54(s,2H, Ar-H),8.17(s,2H,CH).
Compound 91
Gained sterling is yellow solid, yield 92%, m.p.170-172 DEG C;Elementary analysiss/%：Value of calculation：C,C,59.43; H,5.30;N,30.32;Measured value：C,59.65;H,5.44;N,30.24;1H NMR(600MHz,DMSO-d6):δ2.29(s, 3H,CH3),5.18(s,2H,CH2),5.44(s,2H,CH2),6.95(s,2H,NH2),7.41-7.59(m,5H,Ar-H),8.02 (s,1H,CH),8.19(s,1H,CH),8.24(s,1H,CH).
Compound 92
Gained sterling is yellow solid, yield 65%, m.p.214-216 DEG C;Elementary analysiss/%：Value of calculation：C,52.17;H, 4.38;N,30.42;Measured value：C,51.72;H,4.23;N,30.89;1H NMR(600MHz,DMSO-d6):δ2.29(s,3H, CH3),5.26(s,2H,CH2),5.43(s,2H,CH2),6.96(s,2H,NH),7.86(d,2H,J=9.0Hz,Ar-H),8.22 (s,1H,CH),8.27(d,2H,J=8.4Hz,CH),8.42(s,1H,CH).
Compound 93
Gained sterling is yellow solid, yield 32%, m.p.180-182 DEG C;Elementary analysiss/%：Value of calculation：C,52.17;H, 4.38;N,30.42;Measured value：C,52.73;H,4.45;N,30.08;1H NMR(600MHz,DMSO-d6):δ2.30(s,3H, CH3),5.32(s,2H,CH2),5.46(s,2H,CH2),6.96(s,2H,NH2),7.10(t,1H,J=7.2Hz,Ar-H),7.46 (d,1H,J=8.4Hz,Ar-H),7.67(t,1H,J=7.8Hz,Ar-H),7.32(d,1H,J=7.2Hz,Ar-H),7.98(s, 1H,CH),7.99(s,1H,CH),8.27(s,1H,CH).
Compound 94
Gained sterling is yellow solid, yield 46%, m.p.154-155 DEG C;Elementary analysiss/%：Value of calculation：C,53.71;H, 4.51;N,27.40;Measured value：C,53.51;H,4.58;N,27.69;1H NMR(600MHz,DMSO-d6):δ2.29(s,3H, CH3),5.21(s,2H,CH2),5.44(s,2H,CH2),6.94(s,2H,NH),7.44-7.50(m,2H,Ar-H),7.57(d, 1H,J=9.0Hz,Ar-H),7.65(s,2H,CH),7.99(s,1H,CH),8.20(s,1H,CH),8.26(s,1H,CH).
Compound 95
Gained sterling is yellow solid, yield 46%, m.p.154-155 DEG C;Elementary analysiss/%：Value of calculation：C,53.71;H, 4.51;N,27.40;Measured value：C,53.51;H,4.58;N,27.69;1H NMR(600MHz,DMSO-d6):δ2.29(s,3H, CH3),5.21(s,2H,CH2),5.44(s,2H,CH2),6.94(s,2H,NH),7.44-7.50(m,2H,Ar-H),7.57(d, 1H,J=9.0Hz,Ar-H),7.65(s,2H,CH),7.99(s,1H,CH),8.20(s,1H,CH),8.26(s,1H,CH).
Embodiment 8：Compound 96Preparation
By 1mmol2- methyl -4- amino -5- azido-methyl pyrimidine and 1mmol iodo-O- propargyl -4- chloro-acetophenone oxime Ether is dissolved in 5mL anhydrous acetonitrile, adds 0.1mmol Hydro-Giene (Water Science). and 2mmol triethylamine, stirring reaction 12 hours under room temperature condition, The stirring that adds water has solid to separate out, sucking filtration, dry yellow solid, yield 72%；1H NMR(600MHz,DMSO-d6)δ(ppm): 2.16(s,3H,CH3),2.30(s,3H,CH3),5.17(s,2H,CH2),5.45(s,2H,CH2),6.90(s,2H,NH2),7.44 (d,2H,J=8.4Hz,Ar-H),7.66(d,2H,J=8.4,Ar-H).
Compound 97-104 presses compound 96 similar approach and is obtained, and its Structural Identification data is as follows：
Compound 97
Gained sterling is white solid, yield 75%,
1H NMR(600MHz,DMSO-d6)δ(ppm):2.16(s,3H,CH3),2.30(s,3H,CH3),5.16(s,2H, CH2),5.46(s,2H,CH2),6.90(s,2H,NH2),7.22(s,2H,Ar-H),7.70(s,2H,Ar-H).
Compound 98
Gained sterling is white solid, yield 69%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.13(s,3H, CH3),2.29(s,3H,CH3),5.15(s,2H,CH2),5.43(s,2H,CH2),6.90(s,2H,NH2),7.42(s,2H,Ar- H),7.64(s,2H,Ar-H).
Compound 99
Gained sterling is white solid, yield 79%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.16(s,3H, CH3),2.31(s,3H,CH3),5.16(s,2H,CH2),5.46(s,2H,CH2),6.96(s,2H,NH2),7.39(s,3H,Ar- H),7.65(s,2H,Ar-H).
Compound 100
The sterling of gained is white solid, yield 81%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.22(s,3H, CH3),2.33(s,3H,CH3),5.24(s,2H,CH2),5.49(s,2H,CH2),6.94(s,2H,NH2),7.91(d,2H,J= 7.8Hz,Ar-H),8.23(d,2H,J=8.4Hz,Ar-H).
Compound 101
The sterling of gained is white solid, yield 80%,
1H NMR(600MHz,DMSO-d6)δ(ppm):2.16(s,3H,CH3),2.30(s,3H,CH3),5.18(s,2H, CH2),5.44(s,2H,CH2),6.91(s,2H,NH2),7.42(s,1H,Ar-H),7.47(s,1H,Ar-H),7.62(s,1H, Ar-H),7.69(s,1H,Ar-H).EI-MS(m/z,%):497(M+,5.21).
Compound 102
The sterling of gained is white solid, yield 76%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.15(s,3H, CH3),2.31(s,3H,CH3),5.17(s,2H,CH2),5.45(s,2H,CH2),6.91(s,2H,NH2),7.58(s,4H,Ar- H).
Compound 103
The sterling of gained is white solid, yield 78%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.15(s,3H, CH3),2.31(s,3H,CH3),5.17(s,2H,CH2),5.44(s,2H,CH2),6.91(s,2H,NH2),7.22(d,1H,J= 7.8Hz,Ar-H),7.25(d,1H,J=8.4Hz,Ar-H),7.43-7.46(t,2H,J=7.8Hz,7.2Hz,Ar-H),7.65 (s,1H,pyrimidine CH).
Compound 104
The sterling of gained is white solid, yield 74%,1H NMR(600MHz,DMSO-d6)δ(ppm):2.10(s,3H, CH3),2.32(s,3H,CH3),5.19(s,2H,CH2),5.46(s,2H,CH2),7.00(s,2H,NH2),7.34(s,1H,Ar- H),7.50(s,1H,Ar-H),7.70(s,1H,Ar-H).
The compound of above-described embodiment synthesis is shown in Table 1.
The compound of table 1 synthesis
The present invention has formula（I）The compound of structure has excellent bactericidal activity, can be used for preventing and treating wheat scab Bacterium, Rhizoctonia solani Kuhn, botrytis cinerea pers, tomato early blight bacterium, tobacco brown spot pathogen and cucumber anthracnose, part chemical combination Thing is suitable with comparison commercialization antibacterial or more preferable to the prevention effect of funguses.
Embodiment 9 bactericidal activity is tested
Growth rate with mycelia is according to measuring bactericidal activity.Choose and industrial crops, greengrocery crop, fruits Six kinds of relevant common mushrooms of crop：Rice sheath blight disease, gray mold of cucumber, wheat scab, early blight of tomato, Alternaria alternate With cucumber anthracnose as examination target.The compounds of this invention acetone solution, tween 80 emulsifying, add distilled water to be made into one Determine concentration liquid stand-by.200 grams of Rhizoma Solani tuber osi, 15 grams of glucose, 15 grams of agar, after 1000 grams of water is made into culture medium, in diameter 9cm Culture dish high-temperature pressure-reduction sterilizing 25min, while hot culture medium 13.5mL and medicinal liquid 1.5mL mix homogeneously are distributed to two after sterilizing In individual culture dish, horizontal positioned, after cooling, take 5mm to carry disease germs fine jade respectively from the culture fluid of strain with sterilized bacteria taker Fat, puts into mycelia in each culture dish and faces down, every ware puts 2-3 kind bacterium.If two groups of blanks, it is subsequently placed in sterile constant-temperature and is dried 48 hours in case, the diameter measuring bacterial plaque, according to blank, represents drug effect with diameter：Suppression ratio %=（Comparison-process）/ comparison ×100%.
Experiment material：
For trying strain：Fusarium graminearum (Gibberella zeae), botrytis cinerea pers (Botrytis Cinerea), tomato early blight bacterium (Alternaria solania), tobacco brown spot pathogen (Alternaria alternata (Fries) Keissler), cucumber anthracnose (GloeosporiumorbiculareArs).
Test result is shown in Table 2.
The test result of table 2 part of compounds（Test concentrations 100 μ g/g）
The document being related in literary composition is as follows：
Document 1：Karl M.Erixon,Chester L.Dabalos,Finian J.Leeper.Synthesis and biological evaluation of pyrophosphate mimics of thiamine pyrophosphate based on a triazole scaffold.Organic&Biomolecular Chemistry,2008,6,3561-3572.

Claims (4)

1. a kind of 2- methyl -4- amino -5- (replacement -1,2,3-triazoles base) methylpyrimidine derivant is it is characterised in that include tool There is the compound of formula (I-2) structure：
Wherein：
X is oxygen or S；
R1Represent hydrogen；
R2Represent H, halogen, nitro or C1-4Alkyl；
R3Represent H, halogen, nitro, CF3, methoxyl group or C1-4Alkyl, R2With R3Position is interchangeable.
2. 2- methyl -4- amino -5- (replacing -1,2,3- triazolyl) methyl that the formula described in claim 1 (I-2) represents is phonetic The preparation method of piperidine derivatives, is characterized in that making the compound that the compound that logical formula (II) represents is represented with logical formula (IV) react：
R in logical formula (IV)1、R2、R3, X definition respectively with R in formula (I-2)1、R2、R3, X definition identical.
3. 2- methyl -4- amino -5- (replacing -1,2,3- triazolyl) methyl that the formula described in claim 1 (I-2) represents is phonetic The application of piperidine derivatives it is characterised in that：Effective ingredient as antibacterial.
4. 2- methyl -4- amino -5- (replacing -1,2,3- triazolyl) methyl that the formula described in claim 1 (I-2) represents is phonetic The application of piperidine derivatives it is characterised in that：As early to fusarium graminearum, Rhizoctonia solani Kuhn, botrytis cinerea pers, Fructus Lycopersici esculenti The effective ingredient of epidemic disease bacterium, tobacco brown spot pathogen and cucumber anthracnose antibacterial.
CN201410082965.XA 2014-03-07 2014-03-07 2-methyl-4-amino-5-(substituted-1,2,3-triazolyl)methylpyridine derivatives having bactericidal activity, and preparation method and application thereof Active CN104892581B (en)

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