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[ CAS No. 3740-92-9 ]

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Chemical Structure| 3740-92-9
Chemical Structure| 3740-92-9
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CAS No. :3740-92-9 MDL No. :MFCD00754193
Formula : C10H6Cl2N2 Boiling Point : 235.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :225.07 g/mol Pubchem ID :77338
Synonyms :

Safety of [ 3740-92-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3740-92-9 ]

  • Upstream synthesis route of [ 3740-92-9 ]
  • Downstream synthetic route of [ 3740-92-9 ]

[ 3740-92-9 ] Synthesis Path-Upstream   1~11

  • 1
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YieldReaction ConditionsOperation in experiment
84% at 100℃; for 48 h; Green chemistry General procedure: To 40 g of the 2-substituted 6-hydroxy-[3H]-pyrimidin-4-one 4, 300 mL of phosphoryl chloride was added. The mixture was heated for 48 h at 100°C. The excess of phosphoryl chloride was removed by distillation under reduced pressure (20 mbar). Chloroform (200 mL) and ice water (100 mL) were added and the mixture was well stirred for 30 min. The solution was adjusted to pH 5–6 with aqueous sodium carbonate solution. The organic layer was separated and the water phase was extracted three times with 200 mL of chloroform. The combined chloroform phases were dried with magnesium sulfate, filtered, and finally the chloroform was removed under reduced pressure. The obtained crude material was distilled under reduced pressure or purified by column chromatography using silica gel, mesh 60, and chloroform.
71%
Stage #1: for 12 - 16 h; Heating / reflux
Stage #2: With sodium hydrogencarbonate In water
A mixture of compound 2-phenyl-pyrimidlne-4,6-diol (33 g, 175.5 mmol) andPOCl3 (300 ml) was refluxed for 12-16 hours, excess Of POCl3 was distilled out and the crude was neutralized by saturated sodiumbicarbonte solution. The solid obtained was filtered and dried under vacuum to afford the compound 4,6-dichloro-2-phenyl- pyrimidine (28 g, 71percent) as off white solid.
62% for 3 h; Heating / reflux Example 6; Step a: 4,6-Dichloro-2-phenyl-pyrimidine (6a); To a mixture of 2-phenylpyrimidine-4,6-diol (7 g, 0.037 mol) in POCI3 (26 ml,0.279 mol), amine was added slowly (11.8 ml, 0.074 mol). The reaction mixture was heated to reflux for 3h. Some of the POCI3 was evaporated, and the residue was poured on ice followed by extraction with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to give the title compound (5.16 g, 62percent), MS (M+H)+226.
Reference: [1] Patent: US2003/162764, 2003, A1,
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2627 - 2634
[3] Patent: US6372751, 2002, B1, . Location in patent: Example Pr3
[4] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
[5] Farmaco, 1997, vol. 52, # 1, p. 61 - 65
[6] Patent: WO2006/34473, 2006, A2, . Location in patent: Page/Page column 249-250
[7] Patent: WO2008/95999, 2008, A1, . Location in patent: Page/Page column 74
[8] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 2629 - 2634
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YieldReaction ConditionsOperation in experiment
35%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2 h;
Stage #2: at -78℃; for 0.5 h;
4,6-dichloro-2-phenylpyrimidineN-Butyl lithium (3.22 g, 50.3 mmol, and 1.6N in hexane) was added dropwise to a stirred solution of bromobenzene (7.9 g, 50.3 mmol) in THF (70 mL) over a period of 30 min at -78 °C, and reaction was continued stirring for 2 h. The generated phenyl lithium was added dropwise to a stirred solution of 4, 6-dichloropyrimidine (5 g, 33.5 mmol) in THF (50 mL) over a period of 45 min at -78 0C, and reaction was continued stirring for 30 min. Then, the reaction mixture was slowly heated to 0 °C and quenched with water (100 ml), DDQ (7 g, 30. 8 mmol) dissolved in THF (70 mL) was added portionwise and stirred for 10 min. Then, the reaction mixture was washed with 10percent NaOH (50 mL), extracted with CH2Cl2 (3x100 mL), washed with brine (100 mL), dried (Na2SO4) and concentrated. The concentrated product was purified through silica column chromatography using pet. ether to afford 4,6-dichloro-2- phenylpyrmimidine (example 21, 2.6 g, 35 percent) as a white solid. Rf: 0.3 (100percent PE). 1H NMR (400 MHz, CD3OD): δ 8.41-8.39 (m, 2H), 7.60 (s, IH), 7.58-7.50 (m, 3H). m/e (M+l): 224.8.
Reference: [1] Patent: WO2008/154026, 2008, A1, . Location in patent: Page/Page column 88
[2] Patent: WO2008/154026, 2008, A1, . Location in patent: Page/Page column 88
  • 3
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YieldReaction ConditionsOperation in experiment
86.06% at 110℃; for 3 h; The intermediate (1.75 g, 9.30 mmol) was added to a 100 mL round-bottomed flask, and phosphorus oxychloride (3.57 g, 23.23 mmol) in an oil bath at 110 ° C and the progress of the reaction was checked by thin layer chromatography.3 h after the end of the reaction, careful drop of ice water until precipitation precipitation is no longer so far,The reaction mixture, which had been cooled to room temperature, was filtered under reduced pressure, and the resulting precipitated crude product was purified by recrystallization from ethanol to give a pale yellow solid 5 (1.79 g, yield 86.06percent).
Reference: [1] Patent: CN106188014, 2016, A, . Location in patent: Paragraph 0017
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Reference: [1] Patent: CN107417668, 2017, A, . Location in patent: Paragraph 0085; 0086; 0087
  • 5
  • [ 56-05-3 ]
  • [ 71-43-2 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2005, vol. 40, # 9, p. 862 - 874
  • 6
  • [ 1670-14-0 ]
  • [ 3740-92-9 ]
Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
[2] Patent: CN106188014, 2016, A,
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  • [ 5333-86-8 ]
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Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
  • 8
  • [ 100-47-0 ]
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Reference: [1] Australian Journal of Chemistry, 2015, vol. 68, # 5, p. 814 - 824
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Reference: [1] Journal of the Chemical Society, 1952, p. 328,333
  • 10
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  • [ 124-41-4 ]
  • [ 4319-72-6 ]
YieldReaction ConditionsOperation in experiment
81% for 8 h; Cooling with ice; Reflux 4,6-Dichloro-2-phenylpyrimidine (5.0 g, 22.2 mmol) and NaOCH3 (3.6 g, 66.6 mmol) was stirred in methanol (500 mL) on an ice bath for 1 h, then brought to reflux for 7 h.
After evaporation, the white solid was dissolved in DCM (100 mL) and washed with water.
Evaporation of the organic phase yielded 8 (3.98 g, 81percent) as a white solid. 1H NMR (CD3OD): δ 8.39-8.36 (m, 2H), 7.53-7.44 (m, 3H), 6.76 (s, 1H), 4.08 (s, 3H).
13C NMR (CD3OD): δ 172.3, 165.9, 162.2, 137.4, 132.6, 129.5, 129.5, 106.0, 55.0. MS calcd for C11H9ClN2O [M+H]+ 221.0, found: 221.0.
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 23, p. 6595 - 6615
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Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 3, p. 249 - 254
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