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[ CAS No. 57573-59-8 ]

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Chemical Structure| 57573-59-8
Chemical Structure| 57573-59-8
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CAS No. :57573-59-8 MDL No. :MFCD00195328
Formula : C9H7BrN2O Boiling Point : 364.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :239.07 g/mol Pubchem ID :-
Synonyms :

Safety of [ 57573-59-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 57573-59-8 ]

  • Downstream synthetic route of [ 57573-59-8 ]

[ 57573-59-8 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 123-39-7 ]
  • [ 5794-88-7 ]
  • [ 57573-59-8 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: N-Methylformamide; 5-Bromo-2-aminobenzoic acid at 180℃; for 12h; Stage #2: With water 104 2-Amino-5-bromobenzoic acid (5.00 g, 0.023 mol) was reacted with iV- methylformamide (40 ml) at 180 0C for 12 h. The reaction was quenched with H2O and the resulting precipitate was collected by vacuum filtration to give 5.26 g (95%) of a yellow- white solid; m/z 240.
95% In N,N-dimethyl-formamide at 180℃; for 12h; 1 Method 1 6-Bromo-3-methylquinazolin-4(3H)-one 2-Amino-5-bromobenzoic acid (5.00 g, 0.023 mol) was reacted with N-methylformamide (40 ml) at 180° C. for 12 h. The reaction was quenched with H2O and the resulting precipitate was collected by vacuum filtration to give 5.26 g (95%) of a yellow-white solid; m/z 240.
95% at 180℃; for 12h; 3 Method 3; 6-Bromo-3-methylquinazorm-4(3H)-one; 2-Amino-5-bromobenzoic acid (5.00 g, 0.023 mol) was reacted with N- methylformamide (40 ml) at 180 0C for 12 h. The reaction was quenched with H2O and the 5 resulting precipitate was collected by vacuum filtration to give 5.26 g (95%) of a yellow- white solid; m/z 240.
63% for 6.5h; Sealed tube; Reflux; 12.1 Preparation 12: 3-methyl-6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)quinazolin- 4(3H)-one; Step 1 : 6-bromo-3-methylαuinazolin-4(3H)-one; A mixture of 2-amino-5-bromobenzoic acid (250 g, 1.25 mol) and N-methylformamide (1.3 L) was refluxed in a steel bomb reactor for 6.5 h and cooled to room temperature. The mixture was poured over crushed ice, stirred for 2 h and filtered to give 6-bromo-3- methylquinazolin-4(3H)-one (180 g, 63%) as a brown solid. 1 H NMR (500 MHz, METHANOL-O4) δ ppm 3.36 (1 H, m), 3.58 (3 H, s), 7.58 (1 H, d, J=8.5 Hz), 7.90 (1 H, dd, J=8.7, 2.3 Hz), 8.30 (1 H, m).

  • 2
  • [ 660838-05-1 ]
  • [ 57573-59-8 ]
  • [ 878745-39-2 ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate In 1,4-dioxane at 80℃; for 12h; 4 Method 4; ferf-Butyl (4-methyl-3 - [(3 -methyl-4-oxo-3 ,4-dihvdroquinazolm-6-10 vDaminolphenyll carbamate; A stirred mixture of fers-butyl (3-amino-4-methylphenyl)carbamate (Method 2; 3.08 g, 0.0135 mmol), 6-bromo-3-methylquinazolin-4(3H)-one (Method 3; 3.24 g, 0.0135 mmol), Cs2CO3 (13.20 g, 0.0405 mol, 3.0 equiv), BIνAP (841 mg, 1.35 mmol, 5 mol%) in dioxane (50 ml) was treated with Pd2(dba)3 (618 mg, 0.675 mmol). The reaction mixture was heated to15 80 0C for 12 h. The reaction was then quenched with 10% νaOη(aq) and extracted with EtOAc. The organics were dried with NaCl(sat) and then Na2SO4(S). The organics were removed under reduced pressure and the resulting solid was treated with DCM (100 ml). The resulting precipitate was collected by vacuum filtration (3.00 g, 58%); m/z 387.
  • 3
  • [ 18595-18-1 ]
  • [ 57573-59-8 ]
  • [ 951627-58-0 ]
YieldReaction ConditionsOperation in experiment
7% With potassium <i>tert</i>-butylate In 1,4-dioxane at 80℃; for 5h; 18 Method 18 4-Methyl-3-[(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)amino]benzoic acid A mixture of methyl 3-amino-4-methyl benzoate (1.00 g, 6.06 mmol) and 6-bromo-3-methylquinazolin-4(3H)-one (Method 1; 1.45 g, 6.06 mmol)) and KO-t-Bu (1.6 g, 15.15 mmol) in 1,4-dioxane (20 ml) was treated with Pd2(dba)3 (10% mol) and BINAP (20% mol). The reaction mixture was stirred at 80° C. for 5 h. The reaction was cooled to 25° C. and then filtered. The solid was washed with methanol-EtOAc (1:1), and collected by vacuum filtration. The resulting solid was refluxed in methanol and again filtered. The filtrate was concentrated to 40 ml. Upon cooling to 25° C., a precipitate formed which was collected by vacuum filtration. (723 mg). The product was then purified by reverse phase preparative HPLC (0.1% TFA in acetonitrile and water) to give the desired product (7%). NMR: 8.35 (s, 1H); 8.10 (s, 1H); 7.93 (s, 1H); 7.71 (m, 2H); 7.52 (m, 2H); 7.35 (d, 1H); 3.60 (s, 3H); 2.35 (s, 3H); m/z 309.
  • 4
  • [ 951627-59-1 ]
  • [ 57573-59-8 ]
  • [ 951627-57-9 ]
YieldReaction ConditionsOperation in experiment
11% With sodium t-butanolate In toluene at 100℃; for 12h; 9 Example 9 4-Methyl-3-[(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)amino]-N-[2-(trifluoromethyl)pyridin-4-yl]benzamide A solution of 3-amino-4-methyl-N-[2-(trifluoromethyl)pyridin-4-yl]benzamide (Method 26; 70 mg, 0.237 mmol), 6-bromo-3-methylquinazolin-4(3h)-one (Method 1; 57 mg, 0.237 mmol), BINAP (15 mg, 0.023 mmol), and sodium tert-butoxide (0.147 g, 0.711 mmol) in toluene (3 ml) were treated with Pd2(dba)3 (11 mg, 0.012 mmol). The reaction mixture stirred for 12 h at 100° C. The reaction mixture was then filtered through diatomaceous earth and the organics were removed under reduced pressure. Purification by reverse phase Gilson provided the desired product (12 mg, 11%). NMR: 10.89 (s, 1H); 8.64 (d, 1H); 8.57 (s, 1H); 8.31 (s, 1H); 8.06 (d, 1H); 7.87 (s, 1H); 7.72 (d, 1H); 7.63 (d, 1H); 7.48 (s, 3H); 3.47 (s, 3H); 2.28 (s, 3H); m/z 453.
  • 5
  • [ 32084-59-6 ]
  • [ 74-88-4 ]
  • [ 57573-59-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; 113 To 6-bromoquinazotirv4-ol (1.0 g, 4.44 mmol) in 5 mL DMF was added K2CO3 (0.74 gs 5.33 mmol, 1.2 equiv) followed by MeI (0.28 mL, 4.44 mmol, 1.0 equiv). The reaction was allowed to stir at room temperature overnight. The reaction mixture was diluted with H2O (10 mL) and extracted with Et2O (2 x 15 mL). The combined organic extracts was washed with brine, dried over filtered and concentrated. The crude was purified by flash chromatography (10 % to 60 % EtOAc/ hexanes) to yreld 414 mg of the desired product 113a.
  • 6
  • [ 73183-34-3 ]
  • [ 57573-59-8 ]
  • [ 1209485-71-1 ]
YieldReaction ConditionsOperation in experiment
93% With potassium acetate In N,N-dimethyl acetamide at 110℃; for 7h; Inert atmosphere; 12.2 Step 2: 3-methyl-6-(4.4.5.5-tetramethyl-1.3.2-dioxaborolan-2-yl)αuinazolin-4(3H)-one; A mixture of 6-bromo-3-methylquinazolin-4(3H)-one (2 g, 8.3 mmol), bis(pinacolato)diborane (2.43 g, 9.57 mmol), dichloro[1,1 ,'-bis(diphenylphosphino) ferrocene] palladium (II) dichloromethane adduct (0.35 g, 0.11 mmol), 1 ,1 ,'- bis(diphenylphosphino)ferrocene (0.09 g, 0.16 mmol), potassium acetate (2.5 g, 25.5 mmol) and N.N-dimethylsulfoxide (30 ml_) was heated at 110 0C for 7 h under nitrogen atmosphere. The mixture was cooled to room temperature and diluted with ethyl acetate. Water (15 ml_) was added and the layers were separated. The organic layer was washed 3 times with water (15 ml_), washed with brine and dried over sodium sulfate. The organic layer was and concentrated to a black solid. The solid was stirred in a hexane/ diethyl ether mixture to give the title compound (2.2g, 93%) as fine grey powder. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.77 (d, 1 H, J=1.0 Hz), 8.11 (dd, 1 H, J=8.2, 1.6 Hz), 8.04 (s, 1 H), 7.64 (dd, 1 H, J=8.2, 0.4 Hz), 3.57 (s, 3H), 1.34 (s, 12H).
62% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate In 1,4-dioxane at 1120℃; for 2h; Inert atmosphere; 20 A solution of methylquinazolinone lv (2 g, 8.4 mmol) in l,4-dioxane (60 mL) is degassed under nitrogen for 10 minutes. Potassium acetate (2.8 g, 28.6 mmol), (0268) bis(pinacolato)diboron (2.5 g, 9.9 mmol), and [1,1’- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2) (600 mg, 0.82 mmol) are added. The reaction is heated to 120 °C for 12 hours, then cooled to room temperature, and the solid removed by filtration. The filtrate is concentrated, and the residue is purified by flash column chromatography (10% methanol in DCM) to give dioxaborolane xxxiii (1.5 g, 5.2 mmol) in 62% yield.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 1h; Sonication; Cooling with ice; VI Synthesis of 3-Methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)quinazolin-4(3//)- one (Precursor IX). To the 500 mL round-bottom flask were added 6-bromo-3-methylquinazolin-4(3H)- one (10 grams, 41 mmol), bis(pinacolato)diboron (12.7 grams, 50 mmol), Pd(dppf)Cl2*DCM (1.7 grams, 2 mmol), potassium acetate (12.3 grams, 12 mmol) and l,4-dioxane (236 mL). After being briefly stirred for several minutes, the reaction mixture was degassed using sonicator, subject to vacuum and then purged with nitrogen. This vacuum/nitrogen cycle was performed for three times. The reaction mixture was then heated at l00°C. Reaction is complete after 1 hour and no starting material remained according to LCMS. The reaction mixture was filtered through sand using filter paper, concentrated and purified on silica using ethyl acetate and hexanes. The product was obtained in 85% yield. NMR (400 MHz, Chloroform-d): d 8.78 (d, J = 1.5 Hz, 1H), 8.12 (dd, J = 8.1, 1.5 Hz, 1H), 8.07 (s, 1H), 7.66 (d, J = 8.1 Hz, 1H), 3.59 (s, 3H), 1.36 (s, 12H) ppm.
  • 7
  • [ 32084-59-6 ]
  • [ 6214-20-6 ]
  • [ 57573-59-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromoquinazolin-4(3H)-one With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: methyl 4-nitrobenzenesulfonate at 20℃; Cooling with ice; 19 Intermediate 19A: 6-Bromo-3-methylquinazolin-4(3/-/)-oneTo a suspension of 6-bromoquinazolni-4(3/-/)-one (0.5 g, 2.22 mmol) in THF (12 mL) under nitrogen, was added sodium hydride (0.13 g, 3.33 mmol) and reaction stirred for 30 minutes. The reaction was then cooled using an ice bath and methyl 4- nitrobenzenesulfonate (0.48 g, 2.22 mmol) was added. Reaction allowed to warm to room temperature and stirred overnight. Diluted with water and extracted with ethylacetate. Organic layer washed with brine, dried (MgS04) and concentrated under reduced pressure. The resultant crude material was purified by a 25g silica column in 0-10% methanol in DCM (Biotage Snap cartridge) followed by preparative-HPLC and 10 g SCX cartridge to afford 6-bromo-3-methylquinazolin-4(3/-/)-one (0.22 g, 0.90 mmol).MS (ESI) m/z 240.0 [M+H]+ Similarly prepared were:
  • 8
  • [ 141449-85-6 ]
  • [ 57573-59-8 ]
  • [ 1290634-36-4 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate In 1,4-dioxane at 90℃; for 20h; 20 Intermediate 20A: te/f-Butyl 5-(3-methyl-4-oxo-3,4-dihvdroquinazolin-6- yl)hexahvdropyrrolo[3,4-clpyrrole -2(1 HVcarboxylateA mixture of 6-bromo-3-methylquinazolin-4(3/-/)-one (Intermediate 19A) (0.46 g, 1.92 mmol), ie f-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1 /-/) carboxylate (0.49 g, 2.31 mmol), potassium phosphate, tribasic (1 .33g g, 5.77 mmol), 2-dicyclohexylphosphino-2',6'-di-i- propoxy-1 ,1 -biphenyl (26.9 mg, 0.06 mmol) and tris(dibenzyllideneacetone)dipalladium (0) (17.6 mg, 0.02 mmol) in dioxane (10 mL) was heated at 90 °C for 20h. The mixture was diluted with water and the product extracted into dichloromethane. The organic layer was evaporated to dryness, re-dissolved in methanol and purified using a 5g SCX column. The mixture was then further purified on silica (25g SNAP column on SP4). Eluting with dichloromethane to 60/40 dichloromethane/(2M NH3 in methanol) to afford tert-butyl 5-(3- methyl-4-oxo-3,4-dihydroquinazolin-6-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1 /-/)-carboxylate (270 mg, 0.73 mmol).MS (ESI) m/z 371 .2 [M+H]+
  • 9
  • [ 141449-85-6 ]
  • [ 57573-59-8 ]
  • [ 1290634-38-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); ruphos / 1,4-dioxane / 20 h / 90 °C 2: trifluoroacetic acid / dichloromethane
  • 10
  • [ 57573-59-8 ]
  • [ 1396310-22-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / Pd2dba3*CHCl3 / toluene / 100 °C / Inert atmosphere 2: trifluoroacetic acid; water / 0.5 h / 20 °C
  • 11
  • [ 57573-59-8 ]
  • [ 1396311-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / Pd2dba3*CHCl3 / toluene / 100 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 2.2: 0.17 h / 20 °C
  • 12
  • [ 57573-59-8 ]
  • [ 1396310-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / Pd2dba3*CHCl3 / toluene / 100 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C 2.2: 0.17 h / 20 °C 3.1: trifluoroacetic acid; water / 0.5 h / 20 °C
  • 13
  • [ 57573-59-8 ]
  • [ 1396310-76-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / Pd2dba3*CHCl3 / toluene / 16 h / 100 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C 2.2: 2 h
  • 14
  • [ 57573-59-8 ]
  • [ 1396310-77-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium t-butanolate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / Pd2dba3*CHCl3 / toluene / 16 h / 100 °C / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C 2.2: 2 h
  • 15
  • [ 1269421-52-4 ]
  • [ 57573-59-8 ]
  • [ 1396311-65-1 ]
YieldReaction ConditionsOperation in experiment
6.3% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; Inert atmosphere; 2.A 6-Bromo-3-methylquinazolin-4(3H)-one (0.200 g, 0.837 mmol), N- (3-amino-2,4-difluorophenyl)-N-(4-methoxybenzyl)propane-l-sulfonamide (0.310 g, 0.837 mmol), NaOtBu (0.241 g, 2.51 mmol), and Binap-rac (0.0521 g, 0.0837 mmol) were taken up in toluene as a slurry in a sealed vial. Nitrogen gas was bubbled through for 5 minutes, and Pd2dba3 CHCI3 (0.0433 g, 0.0418 mmol) was added. Nitrogen gas was bubbled through for another 10 minutes, and the reaction was heated to 100°C overnight. The reaction was concentrated and partitioned between EtOAc and 0.1N HC1. The organic layer was washed with water and brine, dried over Na2S0 , filtered and concentrated. The crude product was purified by Biotage chromatography with 1% MeOH/EtOAc to give N-(2,4-difluoro-3-(3- methyl-4-oxo-3 ,4-dihydroquinazolin-6-ylamino)phenyl)-N-(4-methoxybenzyl)propane- 1 - sulfonamide (28 mg, 6.3%) as a solid, m/z (APCI-pos) M+l = 429.2.
  • 16
  • [ 1268830-76-7 ]
  • [ 57573-59-8 ]
  • [ 1396310-19-2 ]
YieldReaction ConditionsOperation in experiment
11% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 16h; Inert atmosphere; 1 6-Bromo-3-methylquinazolin-4(3H)-one (0.100 g, 0.418 mmol), N-(3-amino- 4-chloro-2-fluorophenyl)propane-l -sulfonamide (0.112 g, 0.418 mmol), NaOtBu (0.121 g, 1.25 mmol), Binap-rac (0.0260 g, 0.0418 mmol) and Pd2dba3.CHCl3 (0.0216 g, 0.0209 mmol) were suspended in toluene (8 mL). Ar was bubbled through for 10 minutes, and the reaction was heated to 100°C for 16 hours under an Ar balloon. The next morning the reaction mixture was cooled to room temperature and diluted with ethyl acetate (100 mL) and water (30 mL). The pH of the aqueous layer was adjusted to about 6 with AcOH. The reaction mixture was filtered, and the filter cake was washed with ethyl acetate (50 mL). The filtrate was transferred to a separatory funnel, and the layers were separated. The aqueous layer was extracted with ethyl acetate (1 X 50 mL). The combined organics were dried, filtered and concentrated. The crude product was purified by column chromatography, eluting with DCM/ ethyl acetate (2:1), DCM/ ethyl acetate (1:1) to give N-(4-chloro-2-fluoro- 3 -(3 -methyl-4-oxo-3 ,4-dihydroquinazolin-6-ylamino)phenyl)propane- 1 -sulfonamide (0.020 g, 11%) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 9.83 (br s, 1H), 8.42 (br s, 1H), 8.16 (s, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.42 (d, J=8.6 Hz, 1H), 7.32-7.24 (m, 2H), 7.15 (s, 1H), 3.44 (s, 3H), 3.12 (m, 2H), 1.73 (m, 2H), 0.96 (t, J=7.4 Hz, 3H). LC/MS: m/z 425.1, 427.1 [M+l].
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃;
  • 17
  • [ 1016778-99-6 ]
  • [ 57573-59-8 ]
  • [ 1396311-01-5 ]
YieldReaction ConditionsOperation in experiment
19% With (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; sodium t-butanolate In toluene at 120℃; for 0.25h; Microwave reactor; 44.B A sealed microwave vial was charged with 6-bromo-3- methylquinazolin-4(3H)-one (0.075 g, 0.31 mmol), N-(3-amino-4-methylphenyl)propane-l- sulfonamide (0.079 g, 0.35 mmol), Pd2(dba)3 (0.014 g, 0.016 mmol), (R)-BINAP (0.020 g, 0.031 mmol), sodium tert-butoxide (0.106 g, 1.10 mmol) and toluene (2.3 mL). The mixture was heated in a microwave reactor at 120°C for 15 minutes. The reaction mixture was filtered, and the filtrate was directly concentrated in vacuo. The crude product was purified by reverse phase HPLC to give N-(4-methyl-3-(3-methyl-4-oxo-3,4-dihydroquinazolin-6- ylamino)phenyl)propane-l -sulfonamide (23 mg, 19%). 1H NMR (500 MHz, (CD3)2SO) δ 9.58 (s, 1H), 8.14 (s, 1H), 7.94 (s, 1H), 7.53 (d, J = 8.8 Hz, 1H), 7.45 (d, J = 2.6 Hz, 1H), 7.39 (dd, J = 8.8, 2.7 Hz, 1H), 7.18 (d, J = 8.2 Hz, 1H), 7.14 (d, J = 2.1 Hz, 1H), 6.85 (dd, J = 8.1, 2.2 Hz, 1H), 3.46 (s, 3H), 3.02 (dd, J = 8.6, 6.7 Hz, 2H), 2.14 (s, 3H), 1.74 - 1.60 (m, 2H), 0.94 (t, J = 7.5 Hz, 3H); m/z (ES-MS) 387.2 (96.1%) [M+1], LCMS retention time: 3.78 minutes.
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃;
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