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Chemical Structure| 59489-71-3 Chemical Structure| 59489-71-3
Chemical Structure| 59489-71-3

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Product Details of 2-Amino-5-bromopyrazine

CAS No. :59489-71-3
Formula : C4H4BrN3
M.W : 174.00
SMILES Code : C1=C(N=CC(=N1)Br)N
MDL No. :MFCD00235015
InChI Key :KRRTXVSBTPCDOS-UHFFFAOYSA-N
Pubchem ID :599539

Safety of 2-Amino-5-bromopyrazine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362+P364

Application In Synthesis of 2-Amino-5-bromopyrazine

* 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 [ 59489-71-3 ]
  • Downstream synthetic route of [ 59489-71-3 ]

[ 59489-71-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 59489-71-3 ]
  • [ 1062608-42-7 ]
YieldReaction ConditionsOperation in experiment
25.1% With N-iodo-succinimide In 1,4-dioxane at 80℃; for 16 h; To the solution of 2 (10.0 g, 57.47 mmol) in 1,4-dioxane (100 mL) was added N- iodosuccinimide (15.5 g, 68.96 mmol). The reaction mixture was heated to 800 C for 16 h, cooled to RT and concentrated under vacuum to remove 1,4-dioxane. 50 mL of water was added and extracted with dichloromethane (50 mL X 4), washed with water (20 mL X 3), dried over sodium sulfate and concentrated under reduced vacuum. Crude product was purified by flash chromatography using 20-30percent ethyl acetate in petroleum ether to afford compound 2b (4.3 g, 25.1percent). 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 1H), 6.76 (s, 2H).
7.56% With iodine In dimethyl sulfoxide at 20 - 100℃; for 4 h; To a solution of compound (ii) (1.98 g, 11.46 mmol) in DMSO (20 ml) was added iodine crystals (3.49 g, 13.75 mmol) at RT and the resulting mixture was heated to 100°C for 4 h and then stirred at RT for 12 h. Water (20 ml) was then added and the reaction mixture was extracted with ethyl acetate (60 ml X 4). Combined organic layers were washed with water (10 ml X 3), saturated sol. of sodium metabisulphite (5 ml X till Iodine color disappears), Brine solution (10 ml), dried over anhydrous Na2S04 and concentrated under vacuum. The crude material was purified by column chromatography over silica gel 230-400 mesh by using ethyl acetate in petroleum ether as an eluent to yield compound (iii) (260 mg, 7.56percent) as white solid.
References: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8860 - 8871.
[2] Patent: WO2017/9773, 2017, A1, . Location in patent: Page/Page column 19.
[3] Patent: WO2013/121387, 2013, A1, . Location in patent: Page/Page column 30.
 

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