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[ CAS No. 573675-55-5 ]

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2D
Chemical Structure| 573675-55-5
Chemical Structure| 573675-55-5
Structure of 573675-55-5 *Storage: {[proInfo.prStorage]}

Quality Control of [ 573675-55-5 ]

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Product Details of [ 573675-55-5 ]

CAS No. :573675-55-5MDL No. :MFCD06657216
Formula :C8H4BrClN2Boiling Point :339.7°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :243.49Pubchem ID :16780855
Synonyms :

Computed Properties of [ 573675-55-5 ]

TPSA : 25.8 H-Bond Acceptor Count : 2
XLogP3 : 3.2 H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 573675-55-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 573675-55-5 ]

  • Upstream synthesis route of [ 573675-55-5 ]
  • Downstream synthetic route of [ 573675-55-5 ]

[ 573675-55-5 ] Synthesis Path-Upstream   1~3

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YieldReaction ConditionsOperation in experiment
81% at 115℃; for 3.00 h; 20.4 ml (0.12 mol) of   N-ethyldiisopropylamine were slowly added to a suspension of 55.0 g (0.24 mol) of   7-bromo-3H-quinazolin-4-one in 300 ml of   phosphorus oxytrichloride. The reaction mixture was stirred at 115° C. for 3 h and subsequently allowed to come to room temperature. Conventional work-up gave 48.0 g of   7-bromo-4-chloroquinazoline; HPLC/MS (M+H)+=244 as solid
76% for 4.00 h; Reflux 7-bromo-4-chloroquinazoline7-bromoquinazolin-4(3H)-one (1.46 g), ?/,?/-diisopropylethylamine (1.24 ml) and POCI3 (5 ml) were heated at reflux. After 4 hours, the warm product was poured over crushed ice and diluted with DCM. The aqueous layer was extracted with DCM and the combined organic layers were washed with brine and dried over Na2SO4. Evaporation of the organics gave the crude product that was filtered over a pad of silica with EtOAc as eluent. Removal of the solvent gave the title compound in high purity. Yield: 1.21 g (4.93 mmol, 76percent). 1H NMR (250 MHz, CDCI3) ? (ppm) 9.03 (s, 1 H), 8.25 (d, J= 1.9 Hz, 1 H), 8.11 (d, J= 8.9 Hz, 1 H), 7.81 (dd, J= 1.9 Hz, J= 8.9 Hz, 1 H).
Reference: [1] Patent: US2013/12489, 2013, A1. Location in patent: Paragraph 0183
[2] Patent: WO2010/146173, 2010, A1. Location in patent: Page/Page column 16-17
[3] Patent: WO2005/42498, 2005, A2. Location in patent: Page/Page column 43
[4] Chemical Biology and Drug Design, 2018, vol. 92, # 5, p. 1859 - 1866
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YieldReaction ConditionsOperation in experiment
97% Reflux To a solution of 7-bromoquinazolin-4-ol (2.88 g, 12.8 mmol) in POCl3 (30 mL) was added PCl5 (4 g, 19.2 mmol). The mixture was stirred at reflux overnight. After cooling to room temperature, the mixture was concentrated. The residue was dissolved in CH2Cl2 and treated with saturated aqueous NaHCO3 solution. A precipitate that formed was filtered off from the mixture. The organic layer was washed with brine, dried and concentrated to give 7-bromo-4-chloroquinazoline (3 g, 97percent). 1H NMR (DMSO-d6) δ 8.36 (s, IH), 8.01 (d, J- 8.40Hz, IH), 7.88 (d, J = 1.60 Hz, IH), 7.69 (dd, J= 8.80 Hz, 1.60 Hz, IH).
84% for 4.00 h; Reflux Compound 102 (14.4 g) was dissolved in thionyl chloride (50 ml)Adding 1 mL of the catalytic amount of anhydrous DMF,The reaction was refluxed for 4 hours.After completion of the reaction, excess thionyl chloride was distilled off under reduced pressure to give Compound 103. Yield 92.4percent.
Reference: [1] Patent: WO2009/111028, 2009, A1. Location in patent: Page/Page column 48
[2] Patent: CN106317026, 2017, A. Location in patent: Paragraph 0075; 0076; 0077; 0078; 0368-0371
[3] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10554 - 10560
[4] Patent: WO2015/103317, 2015, A1. Location in patent: Page/Page column 313; 314
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Reference: [1] Patent: US2013/12489, 2013, A1
[2] Journal of the American Chemical Society, 2016, vol. 138, # 33, p. 10554 - 10560
[3] Patent: WO2009/111028, 2009, A1
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