Alternatived Products of [ 78706-26-0 ]
Product Details of [ 78706-26-0 ]
| CAS No. : | 78706-26-0 |
MDL No. : | MFCD10000845 |
| Formula : |
C5H2Cl2N4
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | - |
| M.W : |
189.00
|
Pubchem ID : | - |
| Synonyms : |
|
Application In Synthesis of [ 78706-26-0 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Downstream synthetic route of [ 78706-26-0 ]
- 1
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[ 1709-59-7 ]
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[ 78706-26-0 ]
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4-(5-chloro-[1,2,4]triazolo[1,5-<i>a</i>]pyrimidin-7-ylamino)-<i>N</i>,<i>N</i>-dimethyl-benzenesulfonamide
[ No CAS ]
- 2
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[ 2374-05-2 ]
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[ 78706-26-0 ]
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[ 1621983-51-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate In N,N-dimethyl-formamide at 30℃; |
4.1.3 General procedure for the synthesis of N-(4-substituted-phenyl)-7-substituted phenoxy-[1,2,4]triazolo[1,5-a]pyrimidin-5-amines (7a-m) and N5-(4-substituted- phenyl)-N7-substituted-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diamines (7n, 7o)
General procedure: The appropriate substituted phenols or anilines (about 2.7 mmol) were dissolved in anhydrous DMF (15 mL) in the presence of anhydrous K2CO3 (about 5.4 mmol) at room temperature followed by addition of the intermediate 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) (about 3 mmol). The reaction mixture was stirred at 30 °C for 6-12h (monitored by TLC). Then some water was added to the reaction mixture. The formed solid was filtered, washed with water, and dried under vacuum to give the desired intermediates 6(a-h), which were used in the following step without further purification. Yields ranged from 50 to 90%. The mixture of the corresponding intermediate 6(a-h) (about 1.5 mmol) and 4-aminobenzonitrile (about 5.25 mmol) was stirred at 150 °C for about 2h (monitored by TLC) according to the reported method. The mixture was cooled to room temperature, diluted with DMF to get a clear solution, then concentrated with a balanced amount of silica gel in vacuo. Products were purified by column chromatography with ethyl acetate/petroleum ether (1:2) to afford 15 target compounds 7a-o, respectively. Yields ranged from 60 to 80%. |
Reference：
[1]Wang, Liu; Tian, Ye; Chen, Wenmin; Liu, Hong; Zhan, Peng; Li, Dongyue; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Liu, Xinyong
[European Journal of Medicinal Chemistry, 2014, vol. 85, p. 293 - 303]
- 3
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[ 1123-63-3 ]
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[ 78706-26-0 ]
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[ 1621983-53-6 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate; In N,N-dimethyl-formamide; at 30℃; |
General procedure: The appropriate substituted phenols or anilines (about 2.7 mmol) were dissolved in anhydrous DMF (15 mL) in the presence of anhydrous K2CO3 (about 5.4 mmol) at room temperature followed by addition of the intermediate 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) (about 3 mmol). The reaction mixture was stirred at 30 C for 6-12h (monitored by TLC). Then some water was added to the reaction mixture. The formed solid was filtered, washed with water, and dried under vacuum to give the desired intermediates 6(a-h), which were used in the following step without further purification. Yields ranged from 50 to 90%. The mixture of the corresponding intermediate 6(a-h) (about 1.5 mmol) and 4-aminobenzonitrile (about 5.25 mmol) was stirred at 150 C for about 2h (monitored by TLC) according to the reported method. The mixture was cooled to room temperature, diluted with DMF to get a clear solution, then concentrated with a balanced amount of silica gel in vacuo. Products were purified by column chromatography with ethyl acetate/petroleum ether (1:2) to afford 15 target compounds 7a-o, respectively. Yields ranged from 60 to 80%. |
- 4
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[ 78706-26-0 ]
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[ 118-79-6 ]
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[ 1621983-55-8 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate In N,N-dimethyl-formamide at 30℃; |
4.1.3 General procedure for the synthesis of N-(4-substituted-phenyl)-7-substituted phenoxy-[1,2,4]triazolo[1,5-a]pyrimidin-5-amines (7a-m) and N5-(4-substituted- phenyl)-N7-substituted-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diamines (7n, 7o)
General procedure: The appropriate substituted phenols or anilines (about 2.7 mmol) were dissolved in anhydrous DMF (15 mL) in the presence of anhydrous K2CO3 (about 5.4 mmol) at room temperature followed by addition of the intermediate 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) (about 3 mmol). The reaction mixture was stirred at 30 °C for 6-12h (monitored by TLC). Then some water was added to the reaction mixture. The formed solid was filtered, washed with water, and dried under vacuum to give the desired intermediates 6(a-h), which were used in the following step without further purification. Yields ranged from 50 to 90%. The mixture of the corresponding intermediate 6(a-h) (about 1.5 mmol) and 4-aminobenzonitrile (about 5.25 mmol) was stirred at 150 °C for about 2h (monitored by TLC) according to the reported method. The mixture was cooled to room temperature, diluted with DMF to get a clear solution, then concentrated with a balanced amount of silica gel in vacuo. Products were purified by column chromatography with ethyl acetate/petroleum ether (1:2) to afford 15 target compounds 7a-o, respectively. Yields ranged from 60 to 80%. |
Reference：
[1]Wang, Liu; Tian, Ye; Chen, Wenmin; Liu, Hong; Zhan, Peng; Li, Dongyue; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Liu, Xinyong
[European Journal of Medicinal Chemistry, 2014, vol. 85, p. 293 - 303]
- 5
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[ 2432-14-6 ]
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[ 78706-26-0 ]
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[ 1621983-56-9 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With potassium carbonate In N,N-dimethyl-formamide at 30℃; |
4.1.3 General procedure for the synthesis of N-(4-substituted-phenyl)-7-substituted phenoxy-[1,2,4]triazolo[1,5-a]pyrimidin-5-amines (7a-m) and N5-(4-substituted- phenyl)-N7-substituted-phenyl-[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diamines (7n, 7o)
General procedure: The appropriate substituted phenols or anilines (about 2.7 mmol) were dissolved in anhydrous DMF (15 mL) in the presence of anhydrous K2CO3 (about 5.4 mmol) at room temperature followed by addition of the intermediate 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) (about 3 mmol). The reaction mixture was stirred at 30 °C for 6-12h (monitored by TLC). Then some water was added to the reaction mixture. The formed solid was filtered, washed with water, and dried under vacuum to give the desired intermediates 6(a-h), which were used in the following step without further purification. Yields ranged from 50 to 90%. The mixture of the corresponding intermediate 6(a-h) (about 1.5 mmol) and 4-aminobenzonitrile (about 5.25 mmol) was stirred at 150 °C for about 2h (monitored by TLC) according to the reported method. The mixture was cooled to room temperature, diluted with DMF to get a clear solution, then concentrated with a balanced amount of silica gel in vacuo. Products were purified by column chromatography with ethyl acetate/petroleum ether (1:2) to afford 15 target compounds 7a-o, respectively. Yields ranged from 60 to 80%. |
Reference：
[1]Wang, Liu; Tian, Ye; Chen, Wenmin; Liu, Hong; Zhan, Peng; Li, Dongyue; Liu, Huiqing; De Clercq, Erik; Pannecouque, Christophe; Liu, Xinyong
[European Journal of Medicinal Chemistry, 2014, vol. 85, p. 293 - 303]
- 6
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[ 94-64-4 ]
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[ 78706-26-0 ]
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C13H11Cl2N5
[ No CAS ]
- 7
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[ 39959-67-6 ]
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[ 78706-26-0 ]
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C13H11Cl2N5
[ No CAS ]
- 8
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[ 53332-78-8 ]
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[ 78706-26-0 ]
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5-chloro-N-(thiazol-2-ylmethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 80% |
With triethylamine; In 1,4-dioxane; at 25℃;Inert atmosphere; |
General procedure: Example 7. General Procedure G A mixture of the desired chlorotriazolopyrimidines i-G (1 equiv), desired aminomethyl heterocycle or benzylamine ii-G (1.2 equiv), and triethylamine (NEt3) (1.5- 3.5 equiv) in 1,4-dioxane (~0.2 M) was stirred at room temperature until the reaction was complete by LC-MS and/or TLC analysis. The crude reaction mixture was directly purified by silica gel chromatography (typical eluents included either a mixture of hexanes and EtOAc or a mixture of CH2Cl2 and MeOH or an 80:18:2 mixture of CH2Cl2/CH3OH/concentrated NH4OH) to afford the desired product iii-G. The product structures prepared according to General Procedure G were confirmed by 1H NMR and/or by mass analysis. |
- 9
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[ 78706-26-0 ]
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[ 313546-18-8 ]
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4-(5-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-3-methylbenzonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; at 50℃; for 2.0h;Inert atmosphere; |
Step 1: A suspension of 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (CAS 78706-26-0) (1 g, 5.29 mmol), <strong>[313546-18-8](4-cyano-2-methylphenyl)boronic acid</strong> (CAS 313546-18-8, 0.852 g, 5.29 mmol), Na2C03 (0.589 g, 5.56 mmol) and PdCl2(dppf)-CH2Cl2Adduct (0.432 g, 0.529 mmol) in dioxane (30 mL) and water (6 mL) was flushed with N2 and heated to 50 C for 2 h. The reaction was poured into EtOAc and washed with water. The organic was collected, dried (phase separator) and concentrated in vacuo to afford crude 4-(5-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)-3-methylbenzonitrile which was taken directly onto the next step. MS ES+: 270.2 |
- 10
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[ 916792-13-7 ]
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[ 78706-26-0 ]
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4-{5-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl}-2-fluoro-5-methylbenzonitrile
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
|
|
Step l : A solution of <strong>[916792-13-7]4-bromo-2-fluoro-5-methylbenzonitrile</strong> (CAS 916792-13-7) (0.500 g, 2.336 mmol) in THF (1.3 ml) under an atmosphere of N2 was cooled to -15C. Isopropylmagnesium lithium chloride (1.3M in THF) (1.874 mL, 2.437 mmol) was added in a drop wise fashion ensuring the temperature remained below -10C. The reaction was stirred at ~ -15 C for 30 mins. More isopropylmagnesium lithium chloride (1.3M in THF) (0.170 mL, 1.168 mmol) was added in a dropwise fashion ensuring the temp did not exceed -10 C and the reaction was stirred at -15 C for a further 30 mins. A solution of 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (CAS 78706-26-0, 0.397 g, 2.102 mmol) in THF (6.50 mL) was added over 2 mins and the reaction was allowed to warm to rt for 3 days. The reaction was quenched with 2M HC1 and partitioned between EtAOc and water. The organic was collected, washed with brine, dried (phase separator) and concentrated in vacuo. The resulting residue was purified by flash chromatography (0-100% EtOAc in petrol on Si02) to afford 4-{5-chloro-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl}-2-fluoro-5-methylbenzonitrile . MS ES+: 288 |
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