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[ CAS No. 1603-41-4 ]

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Chemical Structure| 1603-41-4
Chemical Structure| 1603-41-4
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CAS No. :1603-41-4 MDL No. :MFCD00006328
Formula : C6H8N2 Boiling Point : 227°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :108.14 g/mol Pubchem ID :15348
Synonyms :

Safety of [ 1603-41-4 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P305+P351+P338-P311 UN#:2811
Hazard Statements:H301+H311+H331-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1603-41-4 ]

  • Upstream synthesis route of [ 1603-41-4 ]
  • Downstream synthetic route of [ 1603-41-4 ]

[ 1603-41-4 ] Synthesis Path-Upstream   1~34

  • 1
  • [ 3510-66-5 ]
  • [ 1603-41-4 ]
YieldReaction ConditionsOperation in experiment
100% With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16 h; Sealed tube General procedure: A mixture of substrate (0.25 mmol), complex 1 (2.5 × 10− 3 mmol), Cs2CO3 (1 mmol), Conc. NH3(aq) (0.5 mL) and TBAB (0.25 mmol) in water (0.5 mL) were loaded in a sealed reaction tube. The reaction temperature was increased to 110–140 °C and the reaction mixture was stirred for 8–24 h. After cooling to RT, the reaction mixture was poured into a saturated NaCl solution, extracted with ethyl acetate and dried over anhydrous MgSO4. After removal of solvents, the residue was re-crystallized or chromatographed on silica gel. All products were characterized by NMR spectroscopy and were consistent with the literature data.
Reference: [1] Catalysis Communications, 2013, vol. 32, p. 28 - 31
[2] Advanced Synthesis and Catalysis, 2009, vol. 351, # 11-12, p. 1722 - 1726
  • 2
  • [ 108-99-6 ]
  • [ 1603-41-4 ]
  • [ 1603-40-3 ]
YieldReaction ConditionsOperation in experiment
1928 g With ammonia; sodium; ethanolamine In toluene at 60 - 170℃; Autoclave; Inert atmosphere; Large scale 1) Add 9021g of toluene, 538g of sodium metal, 70g of ethanolamine and 1900g of 3-picoline to the autoclave. After tightening the autoclave, open the autoclave inlet and the addition port of the dropping tank, and open the dropping tank And the kettle body valve, the hose through the feeding port into the bottom of the tank, with nitrogen replacement air for 1min, closed the lid of the feeding port, warmed to 60 , dropping liquid ammonia, control the pressure in the autoclave 3MPa, the final Liquid ammonia added amount of 600g. Fully respond.2) The temperature was raised to 170 ° C, nitrogen was filled to a pressure of 5 MPa, and the reaction was sufficiently completed. When the pressure in the autoclave increased to 5.5 MPa,Pressure relief to 5MPa, repeat this operation until the pressure inside the reactor does not rise as the end of the reaction, down to room temperature.3) The ammoniated liquid was taken out and slowly added dropwise to water (9 kg). The mixture was stirred and hydrolyzed and extracted, and the mixture was allowed to stand still. After the aqueous phase was extracted again with 3 L of toluene, the oil phases were combined and the oil phase was quantified by gas chromatography.Among them, 1928g of 2-amino-5-methylpyridine and 144g of 2-amino-3-methylpyridine.
Reference: [1] Patent: US2456379, 1946, ,
[2] Patent: CN106496105, 2017, A, . Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030-0035
  • 3
  • [ 1003-73-2 ]
  • [ 1603-41-4 ]
Reference: [1] Heterocycles, 1987, vol. 26, # 8, p. 2065 - 2068
[2] Bioorganic and medicinal chemistry letters, 2000, vol. 10, # 17, p. 1975 - 1978
[3] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 2, p. 465 - 472
[4] Patent: US5332824, 1994, A,
[5] Patent: US5332824, 1994, A,
  • 4
  • [ 108-99-6 ]
  • [ 1603-41-4 ]
Reference: [1] Patent: CN105801472, 2016, A, . Location in patent: Paragraph 0007
[2] Patent: CN107266361, 2017, A,
  • 5
  • [ 18368-64-4 ]
  • [ 1603-41-4 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
  • 6
  • [ 100047-39-0 ]
  • [ 1603-41-4 ]
Reference: [1] Patent: CN107266361, 2017, A, . Location in patent: Paragraph 0025; 0030; 0036; 0038; 0040; 0042
  • 7
  • [ 7757-82-6 ]
  • [ 1603-41-4 ]
Reference: [1] Patent: US5332824, 1994, A,
  • 8
  • [ 1003-73-2 ]
  • [ 75-44-5 ]
  • [ 1603-41-4 ]
Reference: [1] Patent: US5332824, 1994, A,
  • 9
  • [ 1042146-82-6 ]
  • [ 1603-41-4 ]
  • [ 1244954-88-8 ]
Reference: [1] European Journal of Inorganic Chemistry, 2010, # 21, p. 3307 - 3316
  • 10
  • [ 74405-02-0 ]
  • [ 1603-41-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 2, p. 465 - 472
[2] Bioorganic and medicinal chemistry letters, 2000, vol. 10, # 17, p. 1975 - 1978
  • 11
  • [ 1003-73-2 ]
  • [ 1603-41-4 ]
  • [ 1603-40-3 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 12, p. 4554 - 4557
  • 12
  • [ 104712-04-1 ]
  • [ 1603-41-4 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1985, vol. 19, # 7, p. 479 - 481[2] Khimiko-Farmatsevticheskii Zhurnal, 1985, vol. 19, # 7, p. 829 - 832
  • 13
  • [ 17282-00-7 ]
  • [ 762-04-9 ]
  • [ 1603-41-4 ]
  • [ 1042146-82-6 ]
Reference: [1] Synthesis, 2008, # 10, p. 1575 - 1579
  • 14
  • [ 110-86-1 ]
  • [ 1603-41-4 ]
Reference: [1] Patent: CN107266361, 2017, A,
  • 15
  • [ 36172-53-9 ]
  • [ 1603-41-4 ]
Reference: [1] Heterocyclic Communications, 2014, vol. 20, # 1, p. 21 - 23
  • 16
  • [ 1603-41-4 ]
  • [ 2369-19-9 ]
YieldReaction ConditionsOperation in experiment
37% With tetrafluorohydroboric acid; sodium nitrite In water at -10 - 50℃; for 1 h; To a solution of 2-amino-5-methylpyridine (13) (20.0 g, 185 mmol) in fluoroboric acid (50 wtpercent in water, 50 mL), was added portionwise at -10 °C, sodium nitrite (16.6 g, 240 mmol), while maintaining the temperature below 0 °C. The reaction was stirred at 0 °C for 30 min, then at 50 °C for 30 min. After cooling to room temperature, the mixture was basified (pH 9-10) with a saturated aqueous sodium carbonate solution (250 mL) and extracted with dichloromethane (4 x 125 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on alumina (dichloromethane) to give 2-fluoro-5-methylpyridine (14) (7.50 g, 69 mmol) as a yellow oil. Yield 37percent; Rf (Al2O3, dichloromethane) 0.92; IR (NaCl plates) ν 1246, 1379, 1486, 2929 cm-1; 1H NMR (200 MHz, CDCl3) δ 2.25 (s, 3H, CH3), 6.75 (dd, 1H, J = 8.2 Hz, 3JH-F = 3.0 Hz, H-3), 7.52 (m, 1H, H-4), 7.94 (s, 1H, H-6); 13C NMR (50 MHz, CDCl3) δ 17.4 (CH3), 108.8 (d, 2JC-F = 38 Hz, C-3), 130.6 (C-5), 141.7 (d, 3JC-F = 8 Hz, C-4), 147.2 (d, 3JC-F = 14 Hz, C-6), 162.1 (d, 1JC-F = 236 Hz, C-2).
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 345 - 348
[2] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 818 - 838
[3] Journal of the American Chemical Society, 1949, vol. 71, p. 1125
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1667 - 1675
[5] Patent: US5583148, 1996, A,
[6] Journal of Labelled Compounds and Radiopharmaceuticals, 2011, vol. 54, # 6, p. 312 - 317
  • 17
  • [ 108-99-6 ]
  • [ 1603-41-4 ]
  • [ 1603-40-3 ]
YieldReaction ConditionsOperation in experiment
1928 g With ammonia; sodium; ethanolamine In toluene at 60 - 170℃; Autoclave; Inert atmosphere; Large scale 1) Add 9021g of toluene, 538g of sodium metal, 70g of ethanolamine and 1900g of 3-picoline to the autoclave. After tightening the autoclave, open the autoclave inlet and the addition port of the dropping tank, and open the dropping tank And the kettle body valve, the hose through the feeding port into the bottom of the tank, with nitrogen replacement air for 1min, closed the lid of the feeding port, warmed to 60 , dropping liquid ammonia, control the pressure in the autoclave 3MPa, the final Liquid ammonia added amount of 600g. Fully respond.2) The temperature was raised to 170 ° C, nitrogen was filled to a pressure of 5 MPa, and the reaction was sufficiently completed. When the pressure in the autoclave increased to 5.5 MPa,Pressure relief to 5MPa, repeat this operation until the pressure inside the reactor does not rise as the end of the reaction, down to room temperature.3) The ammoniated liquid was taken out and slowly added dropwise to water (9 kg). The mixture was stirred and hydrolyzed and extracted, and the mixture was allowed to stand still. After the aqueous phase was extracted again with 3 L of toluene, the oil phases were combined and the oil phase was quantified by gas chromatography.Among them, 1928g of 2-amino-5-methylpyridine and 144g of 2-amino-3-methylpyridine.
Reference: [1] Patent: US2456379, 1946, ,
[2] Patent: CN106496105, 2017, A, . Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029; 0030-0035
  • 18
  • [ 1003-73-2 ]
  • [ 1603-41-4 ]
  • [ 1603-40-3 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 12, p. 4554 - 4557
  • 19
  • [ 1603-41-4 ]
  • [ 24638-29-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 22, p. 3679 - 3686
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 2806
[3] Patent: US5620978, 1997, A,
  • 20
  • [ 1603-41-4 ]
  • [ 1074-38-0 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 13, p. 4611 - 4614
[2] Advanced Synthesis and Catalysis, 1997, vol. 339, # 4, p. 335 - 339
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 494
[4] Organic Letters, 2012, vol. 14, # 21, p. 5618 - 5620
  • 21
  • [ 1603-41-4 ]
  • [ 23056-40-8 ]
Reference: [1] Patent: EP2366691, 2011, A1,
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 5, p. 985 - 995
  • 22
  • [ 1603-41-4 ]
  • [ 1802-30-8 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2574,2576
  • 23
  • [ 1603-41-4 ]
  • [ 17282-00-7 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; Bromine (11.3 mL, 0.22 mol) was added to a stirred solution of 2-amino-5-picoline (21.63 g, 0.2 mol) and sodium acetate (29.4 g, 0.36 mol) in acetic acid (200 mL) at room temperature. The warm solution was stirred until starting material had been consumed as judged by alumina neutral thin layer chromatography (CH2Cl2). The dark brown solution was diluted with H2O (100 mL) and decolourised with sodium sulphite. The colourless solution was cooled with an ice bath and carefully basified to ~pH 9 with aqueous ammonia. The copious white precipitate was collected by filtration and washed well with portions of H2O (3 x 30 mL). The precipitate was dried in an oven at 110 °C to give 4 (33.7 g, 90percent) as a fluffy white solid. 1H NMR δ (400 MHz, CDCl3) 7.77 (1 H, d, J 1.0, H-6), 7.52 (1 H, d, J 1.5, H-4), 5.21 (2 H, s, NH2), 2.18 (3 H, s, CH3). LCMS (APCI+) 187.9 (MH+ with 79Br, 95percent), 189.9 (MH+ with 81Br, 100percent).
84% With bromine In dichloromethane at 20℃; for 0.5 h; Cooling with ice A three-necked flask was charged with 2-amino-5-methylpyridine (70.0 g, 654 mmol) Dichloromethane (150 mL);Liquid bromine (36.0 mL, 698 mmol) was added to the ice bath. The reaction was stirred at room temperature for 30 minutes. Saturated sodium sulfite solution (100 mL) was added;The aqueous phase was extracted with dichloromethane (100 mL x 3)The organic phases were combined, washed with water (100 mL) and brine (100 mL)Dry over sodium sulfate and filter. Dried to give a yellow solid,Compound 1 (103.0 g, 550 mmol, 84percent).
53%
Stage #1: With hydrogen bromide; acetic acid In chloroform at 50℃; for 0.5 h; Darkness
Stage #2: With bromine In chloroform at 55℃; for 21 h;
Stage #3: With sodium carbonate In chloroform; water
General procedure: A solution of HBr/CH3CO2H (360 g (260 mL), 1.50 mol, 33percent HBr in CH3CO2H) in anhydrous CHCl3 (300 mL) was added over 15 min to a solution of 5-methylpyrazin-2-amine 15 (42 g, 0.38 mmol) in CHCl3 (1 L). The reaction flask was wrapped in aluminum foil and heated to 50 °C for 30 min in the dark whereupon a solution of Br2 (68 g, 0.42 mmol) in CHCl3 (500 mL) was added dropwise over 3 h during which time the internal temperature of the reaction never exceeded 55 °C. After 18 h at 55 °C the solvent was evaporated under reduced pressure. The crude mixture was diluted with water (200 mL) and the pH was adjusted to pH=9 by the addition of solid Na2CO3. The suspension was filtered under vacuum and the filtrate was extracted with EtOAc (1 L.x.5). The combined organic extracts were concentrated under reduced pressure and purified by flash silica gel chromatography eluting with petroleum ether/EtOAc (5:1-->1:1) to give compound 6-bromo-5-methylpyrazin-2-amine 17a (36 g, 50percent) as a light orange solid
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3796 - 3808
[2] Patent: CN107056781, 2017, A, . Location in patent: Paragraph 0008
[3] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[4] Journal fuer Praktische Chemie (Leipzig), 1989, vol. 331, # 3, p. 369 - 374
[5] Tetrahedron, 2011, vol. 67, # 47, p. 9063 - 9066
[6] Heterocycles, 1994, vol. 38, # 3, p. 529 - 540
[7] Tetrahedron Letters, 1995, vol. 36, # 30, p. 5319 - 5322
[8] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 19, p. 2777 - 2782
[9] Patent: US5861419, 1999, A,
[10] Patent: US4246419, 1981, A,
[11] Patent: US4302242, 1981, A,
[12] Patent: US4317913, 1982, A,
[13] Patent: WO2006/25783, 2006, A1, . Location in patent: Page/Page column 143-144
[14] Dyes and Pigments, 2012, vol. 92, # 3, p. 1184 - 1191
  • 24
  • [ 1603-41-4 ]
  • [ 23100-12-1 ]
Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
  • 25
  • [ 1603-41-4 ]
  • [ 21543-49-7 ]
Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
  • 26
  • [ 1603-41-4 ]
  • [ 101990-45-8 ]
Reference: [1] Synthesis, 1994, # 1, p. 87 - 92
  • 27
  • [ 1603-41-4 ]
  • [ 53515-23-4 ]
  • [ 189005-44-5 ]
YieldReaction ConditionsOperation in experiment
82% With sodium carbonate In water at 60℃; for 6 h; Inert atmosphere Water (100 mL), 3-bromo-4- (4-methylphenyl) -4- oxobutanoic acid (25.12 g, 0.093 mol)2-Amino-5-methylpyridine (3) (10.02 g, 0.093 mol)And sodium carbonate (9.86 g, 0.093 mol) were successively added to a 500 mL reaction flask, After mixing,Slowly warmed to an internal temperature of 60 ° C,Nitrogen protection, thermal reaction 6h,Stop the reaction.With 6N hydrochloric acid pH = 0.5 ~ 1,Stirred at room temperature for 30min,No change in pH after the test, adding an equal amount of ethyl acetate,Stir 15min, points to the reservoir,Water layer plus activated carbon 0.5g, 50 decolorization 30min, hot filtration,The filtrate was adjusted with 6N aqueous sodium hydroxide pH = 3.0 ~ 3.5,Precipitation solid, cooled to 0 ~ 5 insulation 1h, suction filtration,The filter cake was rinsed with 50 mL of ice water and dried under vacuum at 80 ° C. for 6 h.21.38 g (HPLC: 99.2percent) of a light yellow solid was obtained in a yield of 82.0percent.
Reference: [1] Patent: CN107383005, 2017, A, . Location in patent: Paragraph 0054; 0055-0063; 0070; 0071; 0072-0079
  • 28
  • [ 1603-41-4 ]
  • [ 68261-97-2 ]
  • [ 189005-44-5 ]
YieldReaction ConditionsOperation in experiment
52% With sodium carbonate In water at 80℃; for 7 h; Inert atmosphere Water (20 mL),3-Chloro-4- (4-methylphenyl) -4-oxobutanoic acid(5.02 g, 0.022 mol),2-Amino-5-methylpyridine (3) (3.58 g, 0.033 mol)And sodium carbonate (2.33 g, 0.022 mol) were successively added to a 100 mL reaction flask,After mixing,Slowly warmed to 80 internal temperature, nitrogen protection,Insulation reaction 7h, stop the reaction.With 6N hydrochloric acid pH = 0.5 ~ 1, Stirred at room temperature for 30min,No change in pH after the test, adding an equal amount of ethyl acetate,Stir 15min, points to the reservoir,Water layer plus activated carbon 0.1g, 50 decolorization 30min, hot filtration,The filtrate was adjusted to pH = 3.0 ~ 3.5 with 6N aqueous sodium hydroxide solution to precipitate a solid,Cooling to 0 ~ 5 insulation 1h, suction filtration, the filter cake with 10mL ice water rinse,80 vacuum drying 6h,3.21 g of pale yellow solid (HPLC: 97.6percent) was obtained in a yield of 52.0percent.
Reference: [1] Patent: CN107383005, 2017, A, . Location in patent: Paragraph 0064; 0065; 0066; 0067; 0068; 0069
  • 29
  • [ 1603-41-4 ]
  • [ 189005-44-5 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 17, p. 4580 - 4583
[2] Organic Letters, 2017, vol. 19, # 9, p. 2226 - 2229
[3] Journal of Pharmacy and Pharmacology, 2018, vol. 70, # 9, p. 1164 - 1173
  • 30
  • [ 1603-41-4 ]
  • [ 149806-06-4 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 36, p. 6033 - 6036
[2] Synthesis, 1994, # 1, p. 87 - 92
[3] Synthesis, 1994, # 1, p. 87 - 92
  • 31
  • [ 1603-41-4 ]
  • [ 153034-78-7 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 818 - 838
  • 32
  • [ 1603-41-4 ]
  • [ 205744-17-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 345 - 348
  • 33
  • [ 1603-41-4 ]
  • [ 202348-55-8 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 18, p. 3957 - 3962
  • 34
  • [ 1603-41-4 ]
  • [ 1023814-35-8 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 13, p. 3460 - 3463
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