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Chemical Structure| 40775-75-5 Chemical Structure| 40775-75-5

Structure of 40775-75-5

Chemical Structure| 40775-75-5

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Product Details of [ 40775-75-5 ]

CAS No. :40775-75-5
Formula : C5H4N4O2
M.W : 152.11
SMILES Code : OC1=CC(N=C2NC=NN21)=O
English Name :7-Hydroxy-[1,2,4]triazolo[1,5-a]pyrimidin-5(3H)-one

Safety of [ 40775-75-5 ]

Application In Synthesis of [ 40775-75-5 ]

* 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 [ 40775-75-5 ]

[ 40775-75-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 40775-75-5 ]
  • [ 78706-26-0 ]
YieldReaction ConditionsOperation in experiment
68% With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline for 1.5h; Reflux;
64% With trichlorophosphate at 95℃; for 2h; 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) Intermediate 2 (1.00 g, 6.6 mmol) was added to phosphorous oxychloride (POCl3) (6.2 mL, 66 mmol) and refluxed at 95 °C for 2 h in a round bottom flask, during which the solution turned dark. Excess POCl3 was removed under reduced pressure and the residue was treated with triturated ice. Potassium carbonate (K2CO3) was slowly added into this ice-water solution to adjust the pH to 8.0 in an ice bath. The mixture was extracted with dichloromethane (CH2Cl2) (3 × 20 mL). Then the combined organic layers were washed with saturated brine (30 mL), subsequently dried over anhydrous Na2SO4, filtered and concentrated to give the crude product 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) as a yellow solid. 3 could be used in the next step without further purification. Yield: 64%, mp: 126-130°C. ESI-MS: m/z 189.3 (M+1), 191.3 (M+3), 193.2 (M+5).
36% With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline at 110℃; for 0.5h; Inert atmosphere; 1-1 Dissolve 1,2,4-triazolo[1,5-a]pyrimidine-5,7-diol (1.50g, 9.86mmol) in 15mL of phosphorus oxychloride, and add N,N-dimethylaniline (2.4mL, 19mmoL), heated to 110°C and reacted for 30 minutes. The reaction solution was cooled to room temperature, 10g ice cubes were slowly added, and the mixture was extracted three times with ethyl acetate and water. The combined organic phase was collected and dried over anhydrous sodium sulfate. The organic solvent was removed under reduced pressure and purified by column chromatography to obtain 5,7 -Dichloro-1,2,4 triazolo[1,5-a]pyrimidine (670 mg, 36%).
With trichlorophosphate at 95℃; for 12h; 4.1.1 General procedure for the synthesis of 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) Compound 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) was synthesized as previously described. Concretely, compound [1,2,4]triazolo[1,5-a]pyrimidine-5,7-diol (2) 6.08 g (40 mmol) was added to 57 mL (600 mmol) of phosphorous oxychloride and heated under reflux for 12 h in a round bottom flask, during which the solid dissolved and hydrogen chloride was evolved. Excess phosphorous oxychloride was removed by distillation at reduced pressure in a steam-bath and the residue triturated with ice water. The mixture was extracted with methylene chloride. Then the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product 5,7-dichloro-[1,2,4]triazolo[1,5-a]pyrimidine (3) as yellow solid, 4.2g, Yield: 50-60%. mp:126-130 °C. ESI-MS: m/z 189.4(M+1), 191.3(M+3), 193.3(M+5); C5H2Cl2N4 (187.9657). Compound 3 was used in the next step without further purification.
With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate at 100℃; 19.2 2) Synthesis of compound 19-2 Compound 19-1 (9.05g, 59.46mmol) was dissolved in phosphorus oxychloride (50.00mL) at room temperature, N,N-dimethylaniline (14.41g, 118.93mmol) was added, and the reaction mixture was stirred at 100°C. 3 hours.After the reaction was completed, the reaction mixture was cooled to room temperature and concentrated under reduced pressure.The obtained residue was diluted with dichloromethane (100 mL), washed with saturated brine (30 mL × 3), the organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.The obtained residue was separated by silica gel column chromatography (petroleum ether/ethyl acetate=2/1) to obtain compound 19-2.
With <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate at 100℃; 19.2 2) Synthesis of compound 19-2 Compound 19-1 (9.05g, 59.46mmol) was dissolved in phosphorus oxychloride (50.00mL) at room temperature, N,N-dimethylaniline (14.41g, 118.93mmol) was added, and the reaction mixture was stirred at 100°C. 3 hours.After the reaction was completed, the reaction mixture was cooled to room temperature and concentrated under reduced pressure.The obtained residue was diluted with dichloromethane (100 mL), washed with saturated brine (30 mL × 3), the organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure.The obtained residue was separated by silica gel column chromatography (petroleum ether/ethyl acetate=2/1) to obtain compound 19-2.
With trichlorophosphate In <i>N</i>,<i>N</i>-dimethyl-aniline at 20 - 100℃; for 3h; 1.2 2) Synthesis of compounds 1-2 At room temperature, compound 1-1 (9.05g, 59.46mmol) was dissolved in phosphorus oxychloride (50mL), N,N-dimethylaniline (14.41g, 118.93mmol) was added, and the reaction mixture was stirred at 100°C for 3 hours. After the reaction is completed, the reaction mixture is cooled to room temperature and concentrated under reduced pressure. The obtained residue was diluted with dichloromethane (100mL), washed with saturated brine (30mL×3), the organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residues were separated by silica gel column chromatography (petroleum ether/ethyl acetate = 2/1) to obtain compounds 1-2

  • 3
  • [ 40775-75-5 ]
  • [ 1469868-37-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 12 h / 95 °C 2: ethanol / 6 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 150 °C
  • 4
  • [ 40775-75-5 ]
  • [ 1469868-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 12 h / 95 °C 2: ethanol / 6 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 150 °C
  • 5
  • [ 40775-75-5 ]
  • [ 1469868-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 12 h / 95 °C 2: ethanol / 6 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 150 °C
  • 6
  • [ 40775-75-5 ]
  • [ 1469868-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 12 h / 95 °C 2: ethanol / 6 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 150 °C
  • 7
  • [ 40775-75-5 ]
  • [ 1469868-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 12 h / 95 °C 2: ethanol / 6 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 150 °C
  • 8
  • [ 40775-75-5 ]
  • [ 1469868-42-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trichlorophosphate / 12 h / 95 °C 2: potassium carbonate / N,N-dimethyl-formamide / 30 °C 3: 2 h / 150 °C
 

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