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Chemical Structure| 5049-61-6 Chemical Structure| 5049-61-6
Chemical Structure| 5049-61-6

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Synonyms: 2-Aminopyrazine; NSC 13147

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Product Details of Pyrazinamine

CAS No. :5049-61-6
Formula : C4H5N3
M.W : 95.10
SMILES Code : NC1=NC=CN=C1
Synonyms :
2-Aminopyrazine; NSC 13147
MDL No. :MFCD00006137
InChI Key :XFTQRUTUGRCSGO-UHFFFAOYSA-N
Pubchem ID :78747

Safety of Pyrazinamine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Pyrazinamine

* 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.

  • Upstream synthesis route of [ 5049-61-6 ]
  • Downstream synthetic route of [ 5049-61-6 ]

[ 5049-61-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 5049-61-6 ]
  • [ 6270-63-9 ]
YieldReaction ConditionsOperation in experiment
53% at 0 - 40℃; for 1 h; Sodium nitrite (3.4 g, 50 mmol, 1.3 eq.) was added in small portionsto 98percent sulfuric acid (15 mL) ice bath, and the mixture was allowed towarm up and heated to 60. When getting clear, the solution wascooled in an ice bath again. A solution of 2-amino-pyrazine (9) (4 g,39.3 mmol, 1 eq.) in 98percent sulfuric acid (15 mL) was added dropwise.The reaction mixture was stirred at 40 for 1 h. After cooling to roomtemperature, it was slowly poured onto crushed ice and stirred until nonitrogen run out. The solution was adjusted to pH 6 with a 40percent solutionof sodium hydroxide, resulting in lots of sodium sulfate which wasfiltered off whereafter. The filtrate was extracted with EA (50 mL×3),and the combined organics were dried (Na2SO4), filtered and concentratedin vacuo to give the product as a white precipitate (6.38 g,53percent).
References: [1] Bioorganic and Medicinal Chemistry, 2019, vol. 27, # 5, p. 748 - 759.
[2] Journal of the Chemical Society, 1947, p. 371.
[3] Journal of the American Chemical Society, 1946, vol. 68, p. 400.
[4] Journal of Biological Chemistry, 1947, vol. 171, p. 321,324.
  • 2
  • [ 5049-61-6 ]
  • [ 70-23-5 ]
  • [ 1286754-14-0 ]
YieldReaction ConditionsOperation in experiment
28.9% at 0 - 30℃; for 4.5 h; Inert atmosphere Pyrazin-2-amine 4a (1 g, 10 mmol) was dissolved in 50 mL of ethylene glycol dimethyl ether, followed by addition of 50 mL of methanol and 3-bromo-2-oxo-propionate (2.30 g, 12 mmol).
After stirring for 4 hours at room temperature, the reaction mixture was cooled to 0 °C and stirred for 30 minutes until a solid precipitated.
The reaction mixture was filtered, and the filter cake was washed with ether (10 mLx3).
The solid was dissolved in 50 mL of anhydrous ethanol and the solution was refluxed for 4 hours.
The reaction mixture was concentrated under reduced pressure, added with 100 mL of dichloromethane, washed successively with saturated sodium carbonate solution (40 mL) and saturated sodium chloride solution (40 mL), dried over anhydrous sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure to obtain ethyl imidazo[1,2-a]pyrazine-3-carboxylate 14a (0.55 g, yield 28.9percent) as a brown solid.
MS m/z (ESI): 192.1 [M+1]
References: [1] Patent: EP2604610, 2013, A1, . Location in patent: Paragraph 0121; 0122.
  • 3
  • [ 5049-61-6 ]
  • [ 64-17-5 ]
  • [ 1113-59-3 ]
  • [ 1286754-14-0 ]
YieldReaction ConditionsOperation in experiment
28.9%
Stage #1: at 20 - 30℃; for 4 h;
Stage #2: for 4 h; Reflux
Step 1
ethyl imidazo[1,2-c]pyrazine-3-carboxylate
Pyrazin-2-amine 4a (1 g, 10 mmol) was dissolved in 50 mL of ethylene glycol dimethyl ether, followed by addition of 50 mL of methanol and 3-bromo-2-oxo-propionate (2.30 g, 12 mmol).
After stirring for 4 hours at room temperature, the reaction mixture was cooled to 0° C. and stirred for 30 minutes until a solid precipitated.
The reaction mixture was filtered, and the filter cake was washed with ether (10 mL*3).
The solid was dissolved in 50 mL of anhydrous ethanol and the solution was refluxed for 4 hours.
The reaction mixture was concentrated under reduced pressure, added with 100 mL of dichloromethane, washed successively with saturated sodium carbonate solution (40 mL) and saturated sodium chloride solution (40 mL), dried over anhydrous sodium sulfate and filtered.
The filtrate was concentrated under reduced pressure to obtain ethyl imidazo[1,2-a]pyrazine-3-carboxylate 14a (0.55 g, yield 28.9percent) as a brown solid.
MS m/z (ESI): 192.1 [M+1]
References: [1] Patent: US2013/131068, 2013, A1, . Location in patent: Paragraph 0176; 0177.
 

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