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Structure of 5521-56-2

Chemical Structure| 5521-56-2

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Product Details of [ 5521-56-2 ]

CAS No. :5521-56-2
Formula : C5H7N3
M.W : 109.13
SMILES Code : CC1=CN=CC(=N1)N
MDL No. :MFCD08235193
InChI Key :UAOOJJPSCLNTOP-UHFFFAOYSA-N
Pubchem ID :12236939

Safety of [ 5521-56-2 ]

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

Application In Synthesis of [ 5521-56-2 ]

* 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 [ 5521-56-2 ]
  • Downstream synthetic route of [ 5521-56-2 ]

[ 5521-56-2 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 930798-25-7 ]
  • [ 5521-56-2 ]
YieldReaction ConditionsOperation in experiment
71% With ammonia In water at 180℃; for 8 h; sealed vessel 60ml) at O0C was added, diethylmalonate (2.1moleq) in THF (60ml) and 2,6- dichloropyrazine (2Og) in THF (40ml). The mixture was then heated to reflux for 18hrs before being allowed to cool and 2M Hydrochloric acid (100ml) added. The resulting two layers were separated and the THF layer partially concentrated under vacuum to give a solution containing 2-(6-chloro-pyrazin-2-yl)-malonic acid diethyl ester. This solution was EPO <DP n="6"/>then cooled to 100C and 2M sodium hydroxide (328ml) added. After stirring for 24hrs the mixture was washed with methyl isobutyl ketone [MIBK] (200ml) and the organic layer discarded. The aqueous layer containing 2-(6-chloro-pyrazin-2-yl)-malonic acid was then added to 6M hydrochloric acid (135ml), maintaining a reaction temperature of 20-25°C to facilitate the decarboxylation.The resulting 6-chloro-pyrazin-2-yl-acetic acid partially precipitated from the mixture, but for ease of isolation was extracted into MIBK (130ml), dried using MgSO4, filtered and evaporated to give a yellow solid. The resulting crude solid 22.4g was then crystallised from methyl-t-butyl ether (MTBE) to give pure 6-chloro-pyrazin-2-yl-acetic acid , 15.4g 67percent yield based on 2,6-dichlorpyrazine.The 6-chloro-pyrazin-2-yl-acetic acid (20.Og) was then treated with aqueous ammonia (120ml) in a sealed vessel at 180°C (35 bar) for 8hrs. The mixture was then cooled to 20°C and water (40ml) added, before being concentrated under vacuum to remove the ammonia. The product was extracted into ethyl acetate and the solution treated with charcoal, before being dried using MgSO4, filtered and evaporated to give 6-methyl-2-pyrazin-2-ylamine as a pale green solid 9.Og, 71percent yield based on 6-chloro-pyrazin-2-yl-acetic acid. Analysis 2-(6-Chloro-pyrazin-2-yl)-malonic acid diethyl esterMS (EI +ve) 273/275 (M+H) IH NMR (CDCl3) :δ 8.7 (IHs), 8.5 (IHs), 4.9 (IHs), 4.2(2x2Hq), 1.2 (2x3Ht).6- Chloro-pyrazin-l-yl-acetic acidMS (EI +ve) 173/175 (M+H)IHNMR (CDCl3) :δ 8.55 (IH s), 8.50 (IH s); 3.9 (2Hs).6-Methyl-2-pyrazin-2-ylamine MS (GC/MS) : 100percent RT 2.0mins, M+H = 110IHNMR (CDC13) : δ 7.8 (IHs), 7.8 (IHs), 4.4 (2H bs), 2.4 (3Hs). Mpt : 124-1250C
References: [1] Patent: WO2007/35153, 2007, A1, . Location in patent: Page/Page column 2; 4-5.
[2] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 5, p. 1451 - 1456.
[3] Patent: WO2007/35154, 2007, A1, . Location in patent: Page/Page column 28-29.
  • 2
  • [ 544-97-8 ]
  • [ 33332-28-4 ]
  • [ 5521-56-2 ]
YieldReaction ConditionsOperation in experiment
28% at 105℃; for 16.25 h; A. 6-Methylpyrazine-2-ylamine. To a solution containing 6-chloro-2- pyrazineamine (5.0 g, 38.75 mmol) in 1,4-dioxane (70 mL) was added [1,3- bis(diphenylphosphino]Ni(II)Cl2 (2.10 g, 38.76 mmol), followed by drop-wise addition of dimethylzinc in toluene (38.75 mL, 2.0 M, 77.50 mmol), over 15 min. The solution was allowed stir at 105 °C for 16 hours. The solution was then condensed under reduced pressure, diluted with ethyl acetate and filtered through celite to remove the nickel salts. The resultant slurry was purified via Biotage silica gel chromatography (0-8percent methanol in dichloromethane) to afford the title compound as an orange solid (1.18 g, 28percent yield). MS (ESI) m/z 1 10.3 [M+ 1]+.
References: [1] Tetrahedron Letters, 2006, vol. 47, # 3, p. 341 - 344.
[2] Patent: WO2008/51493, 2008, A2, . Location in patent: Page/Page column 101.
[3] Patent: WO2008/83070, 2008, A1, . Location in patent: Page/Page column 85.
[4] Patent: US2013/210818, 2013, A1, . Location in patent: Paragraph 0390.
[5] Patent: WO2009/115486, 2009, A1, . Location in patent: Page/Page column 25-26.
[6] Patent: WO2009/115572, 2009, A2, . Location in patent: Page/Page column 117-118.
[7] Patent: WO2004/108692, 2004, A1, . Location in patent: Page 37-38.
  • 3
  • [ 75-16-1 ]
  • [ 33332-28-4 ]
  • [ 5521-56-2 ]
References: [1] Patent: US2015/175616, 2015, A1, . Location in patent: Paragraph 0242; 0243.
[2] Patent: WO2015/100217, 2015, A1, . Location in patent: Page/Page column 99.
[3] Patent: WO2016/10809, 2016, A1, . Location in patent: Paragraph 0279.
[4] Patent: WO2016/172117, 2016, A1, . Location in patent: Page/Page column 32-33.
  • 4
  • [ 74290-66-7 ]
  • [ 5521-56-2 ]
References: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147.
  • 5
  • [ 6761-50-8 ]
  • [ 5521-56-2 ]
References: [1] European Journal of Medicinal Chemistry, 1997, vol. 32, # 3, p. 195 - 203.
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147.
[3] Journal of the American Chemical Society, 1945, vol. 67, p. 802,804.
[4] Journal of Organic Chemistry, 1959, vol. 24, p. 345,348.
  • 6
  • [ 38557-71-0 ]
  • [ 5521-56-2 ]
References: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1580,1582.
  • 7
  • [ 33332-28-4 ]
  • [ 5158-46-3 ]
  • [ 5521-56-2 ]
References: [1] Tetrahedron Letters, 2006, vol. 47, # 3, p. 341 - 344.
  • 8
  • [ 20721-18-0 ]
  • [ 5521-56-2 ]
References: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1580,1582.
  • 9
  • [ 13401-38-2 ]
  • [ 5521-56-2 ]
References: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 802,804.
  • 10
  • [ 13401-38-2 ]
  • [ 5521-56-2 ]
References: [1] European Journal of Medicinal Chemistry, 1997, vol. 32, # 3, p. 195 - 203.
 

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Technical Information

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