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[ CAS No. 1374208-34-0 ] {[proInfo.proName]}

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Chemical Structure| 1374208-34-0
Chemical Structure| 1374208-34-0
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Product Details of [ 1374208-34-0 ]

CAS No. :1374208-34-0 MDL No. :
Formula : C12H11BrClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 328.59 Pubchem ID :-
Synonyms :

Safety of [ 1374208-34-0 ]

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Application In Synthesis of [ 1374208-34-0 ]

* 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.

  • Downstream synthetic route of [ 1374208-34-0 ]

[ 1374208-34-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 110-91-8 ]
  • [ 959237-68-4 ]
  • [ 1374208-34-0 ]
YieldReaction ConditionsOperation in experiment
84% In dichloromethane; at 0℃; for 0.5h; Step 6: 7-Bromo-2-chloro-4-morpholin-4-yl-quinazolineTo an ice cold solution of 7-bromo-2,4-dichloro-quinazoline (7 g, 0.0255 mol) in DCM (150 mL), morpholine (4.43 mL, 0.0509 mol) was slowly added and the reaction was continued at 0 C for 30 min. The solvent was evaporated to dryness to get the crude compound. The crude product was purified, using column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to get the title compound (7 g, 84%). 1H NMR (300 MHz, CDCls): delta 8.17 (d, J = 7.5 Hz, 1H), 8.04 (d, J = 7.5 Hz, 1H), 7.63 (d, J = 8.1 Hz, 1H), 3.72-3.74 (m, 8H): LC-MS (ESI): Calculated mass: 327.0; Observed mass: 329.8 [M+H]+ (RT: 0.45 min)
84% In dichloromethane; at 0℃; for 0.5h; To an ice cold solution of 7-bromo-2,4-dichloro-quinazoline (7 g, 0.0255 mol) in dichloromethane (150 mL), morpholine (4.43 mL, 0.0509 mol) was slowly added and the reaction was continued at 0 C. for 30 minutes. The solvent was evaporated to dryness to provide the crude compound. The crude product was purified using column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to provide the title compound (7 g, 84%). 1H NMR (300 MHz, CDCl3): delta 8.17 (d, J=7.5 Hz, 1H), 8.04 (d, J=7.5 Hz, 1H), 7.63 (d, J=8.1 Hz, 1H), 3.72-3.74 (m, 8H): LC-MS (ESI): Calculated mass: 327.0; Observed mass [M+H]+: 329.8. (RT: 0.45 min).
Reference： [1]Patent: WO2012/58671,2012,A1 .Location in patent: Page/Page column 93
[2]Patent: US2014/38952,2014,A1 .Location in patent: Page/Page column 0162-0163
  • 2
  • [ 1374208-34-0 ]
  • [ 109299-78-7 ]
  • [ 1374208-35-1 ]
YieldReaction ConditionsOperation in experiment
75% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 95℃; for 2.16667h;Inert atmosphere; Step 7: 2-Chloro-4-morpholin- -yl-7-pyrimidin-5-yl-quinazolineTo a 50 mL round bottom flask, 7-bromo-2-chloro-4-morpholin-4-yl-quinazoline (0.2 g, 0.0006 mol), pyrimidine-5-boronic acid (0.068 g, 0.0005 mol), sodium carbonate (0.129 g, 0.0012 mol), DMF (10 mL) and water (3 mL) were added and degassed the reaction vessel with N2 for 5-10 min. To the same reaction mixture, Pd(PPh3)2Cl2 (0.029 g, 0.00004 mol) was added and again degassed with N2 for 5-10 min. The reaction mixture was stirred at 95C for 2 h. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford the crude product. The crude product was purified; using column chromatography (60-120 silica gel, 60% ethyl acetate in hexane) to yield the desired product [ 150 mg, 75%] . 1H NMR (300 MHz,CDCI3): delta 9.27 (s, 1H), 9.04 (s, 2H), 7.85-8.45 (m, 2H), 7.60-7.64 (m, 1H), 3.82-3.91 (m, 8H); LC-MS (ESI): Calculated mass: 327.09; Observed mass: 328.0 [M+H]+ (RT: 0.98 min).
Reference： [1]Patent: WO2012/58671,2012,A1 .Location in patent: Page/Page column 93-94
  • 3
  • [ 114703-12-7 ]
  • [ 1374208-34-0 ]
Reference： [1]Patent: WO2012/58671,2012,A1
[2]Patent: US2014/38952,2014,A1
  • 4
  • [ 1374208-34-0 ]
  • [ 373384-18-0 ]
  • [ 1374208-37-3 ]
YieldReaction ConditionsOperation in experiment
80% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 90℃; for 2.33333h;Inert atmosphere; Step 1: 2-Chloro-7-(3-methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolineTo a 50 mL round bottom flask, 7-bromo-2-chloro-4-morpholin-4-yl-quinazoline (0.65 g, 0.0019 mol), 3-methylsulfonylphenylboronic acid (0.35 g, 0.0018 mol), sodium carbonate (0.314 g, 0.0029 mol), DMF (25 mL) and water (6 mL) were added and degassed the reaction vessel with nitrogen for 5-10 min. To the same reaction mixture, Pd(PPh3)2Cl2 (0.069 g, 0.00099 mol) was added and again degassed with nitrogen for 5- 10 min. The reaction mixture was stirred at 95 C for 2 h. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford the crude product. The crude product was purified; using column chromatography (60- 120 silica gel, 50% ethyl acetate in hexane) to yield the desired product [400 mg, 80%]. LC-MS (ESI): Calculated mass: 403.1; Observed mass: 404.0 [M+H]+ (RT: 1.36 min).
65% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In water; N,N-dimethyl-formamide; at 95℃; for 2.0h;Inert atmosphere; To a 50 mL round bottom flask, 4-(7-bromo-2-chloroquinazolin-4-yl)morpholine (0.25 g, 0.0007 mol-Preparation 1), 3-methylsulfonylphenylboronic acid (0.137 g, 0.0006 mol), sodium carbonate (0.121 g, 0.00105 mol), DMF (8 mL) and water (2 mL) were added. The reaction vessel was degassed with N2 for 5-10 minutes. To the same reaction mixture, Pd(PPh3)2Cl2 (0.027 g, 0.000035 mol) was added and the mixture again degassed with N2 for 5-10 minutes. The reaction mixture was stirred at 95 C. for 2 hours. The reaction mixture was cooled and water was added. The crude product was extracted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed under the reduced pressure to afford the crude product. The crude product was purified by column chromatography (60-120 silica gel, 50-100% ethyl acetate in n-hexane) to provide the desired product (0.2 g, 65%). 1H NMR (300 MHz, CDCl3): delta 8.25 (br s, 1H), 8.06-7.94 (m, 3H), 7.75-7.46 (m, 3H), 3.93 (br s, 4H), 3.91 (br s, 4H), 3.12 (s, 3H): LC-MS (ESI): Calculated mass: 403.0; Observed mass [M+H]+: 404.0 (RT=1.30 min).
Reference： [1]Patent: WO2012/58671,2012,A1 .Location in patent: Page/Page column 98-99
[2]Patent: US2014/38952,2014,A1 .Location in patent: Page/Page column 0189-0190
  • 5
  • [ 1374208-34-0 ]
  • [ 338998-93-9 ]
  • [ 1374208-36-2 ]
YieldReaction ConditionsOperation in experiment
70% With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; N,N-dimethyl-formamide; at 90℃; for 2.33333h;Inert atmosphere; Step 1: 2-Chloro-7-(5-methyl-furan-2-yl)-4-morpholin-4-yl-quinazolineTo a 50 mL round bottom flask, 7-bromo-2-chloro-4-morpholin-4-yl-quinazoline (2 g, 0.0061 mol), 5-methyl-2-furanboronicacid pinacol ester (1.1 g, 0.0091 mol), sodium carbonate (0.969 g, 0.0092 mol), DMF (80 mL) and water (20 mL) were added and degassed the reaction vessel with nitrogenfor 5-10 min. To the same reaction mixture,Pd(PPh3)2Cl2 (0.213 g, 0.0003 mol) was added and again degassed with nitrogen for 5-10 min. The reaction mixture was stirred at 95 C for 2 h. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford the crude product. The crude product was purified; using column chromatography (60-120 silica gel, 0-20% ethyl acetate in hexane) to yield the desired product [1.4 g, 70%]. 1H NMR: (400 MHz, CDCI3): delta 8.01 (d, J = 1.6 Hz, 1H), 7.80 (d, J = 8.8 Hz, 1H), 7.68 (dd, J = 8.8 Hz, J" = 1.6 Hz, 1H), 6.78 (d, J = 3.2, 1H), 6.14-6.45 (m, 1H), 3.88 (m, 8H), 2.42 (s, 3H); LC-MS (ESI): Calculated mass: 329.1; Observed mass: 330.0 [M+H]+ (RT: 1.71 min).
Reference： [1]Patent: WO2012/58671,2012,A1 .Location in patent: Page/Page column 95-96

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