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Chemical Structure| 19838-08-5

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Product Details of [ 19838-08-5 ]

CAS No. :19838-08-5
Formula : C5H7N3
M.W : 109.13
SMILES Code : NC1=NC=CN=C1C
MDL No. :MFCD08705770
InChI Key :VQPHZDDLWFHRHR-UHFFFAOYSA-N
Pubchem ID :302284

Safety of [ 19838-08-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 19838-08-5 ]

* 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.

  • Upstream synthesis route of [ 19838-08-5 ]

[ 19838-08-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 95-58-9 ]
  • [ 19838-08-5 ]
YieldReaction ConditionsOperation in experiment
89% With ammonia In water at 160℃; for 24 h; Alkaline aqueous solution A mixture of 2-chloro-3-methylpyrazine (7 g, 54.69 mmol) and 25percent NH3.H2O (100 mL) was heated to 1600C for 24h in a sealed tube. The resulting solution was cooled to RT and extracted with EtOAc (3x200 mL). The organics were combined, dried over Na2SO4, and concentrated under vacuum to afford 2.18 g (89percent) of 3-methylpyrazin-2-amine as a yellow solid. LCMS: 110 (M+H)+.
36% With ammonia In methanol at 150℃; for 8 h; In an autoclave, 2-chloro-3-methyl-pyrazine (1) (10.0 g, 77.8 mmol) was dissolved in dry methanol (30 mL). Ammonia gas (60 g) was added. The mixture was heated to 150°C for 8 hours. (start pressure: 10 bar, end pressure: 90 bar). After cooling to rt, the mixture was evaporated to a brown solid, which was dissolved in IN hydrochloric acid (100 mL) and washed with dichloromethane. The aqueous layer was slowly poured on cold saturated aqueous ammonia (150 mL), then extracted with dichloromethane (3 x 100 mL). The combined organic layers were dried (Na2SO4) and evaporated. The product was extracted from the residual solid with hot acetone (200 mL). Evaporation yielded 36 percent of 3-methyl-pyrazin-2- ylamine (2) as a yellow solid
36%
Stage #1: With ammonia In methanol at 150℃; for 8 h;
Stage #2: With hydrogenchloride In methanol; water at 20℃;
Stage #3: With ammonia In methanol; water at 20℃;
In an autoclave, 2-chloro-3-methyl-pyrazine (1) (10.0 g, 77.8 mmol) was dissolved in dry methanol (30 mL) . Ammonia gas (60 g) was added. The mixture was heated to 15O0C for 8 hours, (start pressure: 10 bar, end pressure: 90 bar) . After cooling to rt, the mixture was evaporated to a brown solid, which was dissolved in IN hydrochloric acid (100 mL) and washed with dichloro- methane . The aqueous layer was slowly poured on cold saturated aqueous ammonia (150 mL) , then extracted with dichloromethane (3 x 100 mL) . The combined organic layers were dried (Na2SO4) and evaporated. The product was extracted from the residual solid with hot acetone (200 mL) . Evaporation yielded 36 percent of 3-methyl-pyrazin-2- ylamine (2) as a yellow solid.
References: [1] Patent: WO2009/29625, 2009, A1, . Location in patent: Page/Page column 67.
[2] Patent: WO2005/120513, 2005, A1, . Location in patent: Page/Page column 15; 16.
[3] Patent: WO2006/131003, 2006, A1, . Location in patent: Page/Page column 17.
[4] Synthesis, 1994, # 9, p. 931 - 934.
[5] Patent: WO2010/83617, 2010, A1, . Location in patent: Page/Page column 62.
[6] Patent: EP1790650, 2007, A1, . Location in patent: Page/Page column 60.
[7] Patent: CN107312007, 2017, A, . Location in patent: Paragraph 0007; 0012; 0013.
  • 2
  • [ 74290-67-8 ]
  • [ 19838-08-5 ]
References: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 143 - 147.
  • 3
  • [ 95-58-9 ]
  • [ 19838-08-5 ]
References: [1] Patent: US5861401, 1999, A, .
 

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Technical Information

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