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Chemistry
Organic Building Blocks
Amines
5-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine
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[ CAS No. 1454653-85-0 ] {[proInfo.proName]}

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Chemical Structure| 1454653-85-0
Chemical Structure| 1454653-85-0
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Quality Control of [ 1454653-85-0 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1454653-85-0 ]

CAS No. :1454653-85-0 MDL No. :MFCD27634960
Formula : C5H4ClN5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 169.57 Pubchem ID :-
Synonyms :

Safety of [ 1454653-85-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1454653-85-0 ]

* 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 [ 1454653-85-0 ]

[ 1454653-85-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 894807-98-8 ]
  • [ 1454653-85-0 ]
  • [ 1454654-27-3 ]
YieldReaction ConditionsOperation in experiment
96.77% With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; at 120℃; for 0.75h;Microwave irradiation; 13.3 5-[1-(2-trimethylsilanyl-ethoxymethyl)-1 H-pyrazol-4-yl]- [1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine To a solution of 5-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine (0.3 g, 1.77 mmol) in 1 ,2-dimethoxyethane/water (9:1, 10 ml), 4-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1 H-pyrazole (0.86 g, 2.66 mmol), tetrakis(triphenylphosphine) palladium(O) (0.061 g, 0.05 mmol) and sodium bicarbonate(0.44 g, 5.32 mmol) are added, degassed briefly and irradiated in microwave at 120°C for 45 minutes. The reaction mixture is passed through celite, washed with dichloromethane/methanol (1:1, 25ml), the filtrate is concentrated and purified by silica column using (230-400) mesh to get the product as off white solid (0.09 g, 96.77 percent); TLC: chloroform/methanol (9.5/0.5) Rf- 0.2; 1H NMR: 400 MHz, DMSO-d6: delta [ppm] 8.97 (s, 1H), 8.69 (s, 1H), 8.56 (s, 1H), 8.55(s, 1H), 6.55 (br s, 2H), 5.54 (s, 2H), 3.58 (t, J = 8.12 Hz, 2H), 0.85 (t, J = 8.00 Hz, 2H), -0.051 (s, 9H); LCMS: Mass found (M+, 332.3); Method: A-0.1percent TFA in H20, B-0.1percent TFA in ACN: Flow - 2.0 ml/min. Column: XBridge C8 (50 X 4.6 mm, 3.5 pm), +ve mode Rt (min): 3.92 area percent -74.45 (Max).
Reference： [1]Patent: WO2013/131609,2013,A1 .Location in patent: Page/Page column 112; 113
  • 2
  • [ 590418-08-9 ]
  • [ 1454653-85-0 ]
  • [ 1454653-84-9 ]
YieldReaction ConditionsOperation in experiment
42% With palladium diacetate; potassium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; water; at 110℃; for 10h; 1.1 -(1-methyl-1 H-indazol-5-yl)-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine To a solution of 5-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine (2.0 g, 1 1.8 mmol) in 1 ,4-dioxane/water (9:1, 50 ml_), 1-methyl-1H-indazole-5yl-boronic acid (3.1 g, 17.7 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.4 g, 0.7 mmol)), palladium acetate (0.08 g, 0.35 mmol) and potassium carbonate (4.9 g, 35.4 mmol) are added and heated in a pressure tube at 110 C for 10 h. After completion of the reaction (monitored by TLC), the reaction mixture is passed through celite, washed with dichloromethane/methanol (1 :1 , 75 mL), the filtrate is concentrated to get the crude product. The crude product is purified by column chromatography (silica gel, MEOH/DCM gradient elution); yield: 42 % (1.3 g, yellow solid); LCMS: (Method A) 266.2 (M+H), RT. 2.2 min, 80.3 % (Max), 92.7 % (254 nm); 1H NMR (400 MHz, DMSO-d6): delta [ppm] 8.80 (s, 1H), 8.54 (s, 1H), 8.24-8.21 (m, 2H), 8.03-8.01 (m, 1H), 7.82 (d, J = 8.84 Hz, 1H), 6.53 (br s, 2H), 4.11 (s, 3H).
Reference： [1]Patent: WO2013/131609,2013,A1 .Location in patent: Page/Page column 77
  • 3
  • [ 16182-04-0 ]
  • [ 33332-28-4 ]
  • [ 1454653-85-0 ]
YieldReaction ConditionsOperation in experiment
71.42% 13.1 5-chloro-[1 ,2,4]triazolo[1 ,5-a]pyrazin-2-ylamine To a solution of <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (15.0 g, 115.8 mmol) in dry tetrahydrofuran (150 ml), ethoxycarbonylisothiocyante (16.7g, 127.4 mmol) is added and heated to 50°C for 12 hours. The reaction mixture is concentrated and suspended in ethanol/methanol (1:1 , 300 ml), hydroxylamine hydrochloride (40.09 g, 576.9 mmol) and diisopropylethylamine (44.73 g, 346.1 mmol) are added and heated to 80°C for 3 hours. The reaction mixture is concentrated and the crude mass is taken in water and filtered, washed with water, cold acetonitrile, diethylether, to get the product as pale yellow solid (14.0 g, 71.42 percent); TLC: chloroform/methanol (9.5/0.5) Rf- 0.2. 1H NMR: 400 MHz, DMSO-d6: delta [ppm] 8.80 (s, 1H), 8.18 (s, 1 H), 6.75 (br s, 2H); LCMS: Mass found (M+, 170.0) Method: A-0.1percent TFA in H20, B-0.1percent TFA in ACN: Flow - 1.0 ml/min. Column: XBridge C8 (50 X 4.6 mm, 3.5 pm), +ve mode Rt (min): 2.01 area percent -99.66 (Max), 99.51 (220 nm); HPLC Method: A- A-0.1percent TFA in H20, B- percent TFA in ACN: Flow - 1.0ml/min. Column: XBridge C8 (50 X 4.6 mm, 3.5 pm) Rt (min): 2.02 area percent - 99.23 (Max), 99.05 (220nm).
Reference： [1]Patent: WO2013/131609,2013,A1 .Location in patent: Page/Page column 111; 112

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