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[ CAS No. 57356-64-6 ]

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Chemical Structure| 57356-64-6
Chemical Structure| 57356-64-6
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Product Details of [ 57356-64-6 ]

CAS No. :57356-64-6 MDL No. :MFCD00483257
Formula : C9H12BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :242.12 g/mol Pubchem ID :-
Synonyms :

Safety of [ 57356-64-6 ]

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
GHS Pictogram:

Application In Synthesis of [ 57356-64-6 ]

  • Downstream synthetic route of [ 57356-64-6 ]

[ 57356-64-6 ] Synthesis Path-Downstream   1~15

YieldReaction ConditionsOperation in experiment
2-Piperidinopyrimidin, Br2;
  • 2
  • [ 110-89-4 ]
  • [ 32779-36-5 ]
  • [ 57356-64-6 ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane at 20℃; for 1h; 5 INTERMEDIATE 5; 5-bromo-2-piperidin-l-ylpyrimidine; 2-chloro-5-bromopyrimidine (3g, 15.5 mmol), piperidine (5.3 g, 62 mmol), and DME (30 mL) were stirred at room temperature for 1 hour. The reaction was extracted with methylenechloride and washed with water three times and the solvent evaporated to yield and off white solid.
With triethylamine In tetrahydrofuran at 20℃; 8.I To solution of 5-bromo-2-chloro-pyrimidine (3.0 g, 15.5 mmol) in dichloromethane (30 imL) at room temperature was added piperidine (1.53 mL, 15.5 mmol) followed by the dropwise addition of triethylamine (3.23 mL, 23.3 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with dichloromethane (20 mL), washed with a saturated aqueous sodium bicarbonate solution (50 mL), followed by brine (50 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 5% ethyl acetate in hexanes) provided 5-bromo-2-piperidin-1-yl-pyrimidine as a white solid (3.74g, 15.5 mmol).
With triethylamine In dichloromethane at 20℃; 17; 8.I To solution of 5-bromo-2-chloro-pyrimidine (3.0 g, 15.5 mmol) in dichloromethane (30 mL) at room temperature was added piperidine (1.53 mL, 15.5 mmol) followed by the dropwise addition of triethylamine (3.23 mL, 23.3 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with dichloromethane (20 mL), washed with a saturated aqueous sodium bicarbonate solution (50 mL), followed by brine (50 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 5% ethyl acetate in hexanes) provided 5-bromo-2-piperidin-1-yl-pyrimidine as a white solid (3.74g, 15.5 mmol).
With triethylamine In dichloromethane at 20℃; 8.I To solution of 5-bromo-2-chloro-pyrimidine (3.0 g, 15.5 mmol) in dichloromethane (30 mL) at room temperature was added piperidine (1.53 mL, 15.5 mmol) followed by the dropwise addition of triethylamine (3.23 mL, 23.3 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with dichloromethane (20 mL), washed with a saturated aqueous sodium bicarbonate solution (50 mL), followed by brine (50 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 5% ethyl acetate in hexanes) provided 5-bromo-2-piperidin-1-yl-pyrimidine as a white solid (3.74g, 15.5 mmol).
With triethylamine In dichloromethane at 20℃; 8.I Part I: Preparation of 5-bromo-2-piperidin-1-yl-pyrimidineTo solution of 5-bromo-2-chloro-pyrimidine (3.0 g, 15.5 mmol) in dichloromethane (30 mL) at room temperature was added piperidine (1.53 mL, 15.5 mmol) followed by the dropwise addition of triethylamine (3.23 mL, 23.3 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with dichloromethane (20 mL), washed with a saturated aqueous sodium bicarbonate solution (50 mL), followed by brine (50 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Flash chromatography (silica gel; 5% ethyl acetate in hexanes) provided 5-bromo-2-piperidin-1-yl-pyrimidine as a white solid (3.74g, 15.5 mmol).
In ethanol at 80℃; Sealed tube;
With triethylamine In toluene at 20℃; for 24h; 32 Piperidine (5.1 MI, 51.6 MMOL) was added to a stirred solution of 5-bromo-2-chloropyrimidine (5 g, 25.8 MMOL) and triethylamine (9.0 MI, 64.5 MMOL) in toluene (30 ML). After stirring at room temperature for 24 hours the reaction mixture was diluted with ethyl acetate and washed with 2N hydrochloric acid, brine and dried (magnesium sulfate). The organic layer was filtered, concentrated in vacuo and the resulting residue was purified by column chromatography eluting with ethyl acetate to afford the title compound (D32).

  • 3
  • [ 1066-54-2 ]
  • [ 57356-64-6 ]
  • C14H21N3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; triethylamine In toluene at 100℃; for 12h; 6 INTERMEDIATE 6; 5-ethynyl-2-piperidin-l-ylpyrimidine; 2-piperidyl-5-bromopyrimidine (3.5 g, 15 mmol), TMS acetylene (2.1 g, 29 mmol), Palladium tetrakis(triphenylphosphine) (0.3 g, 0.3 mmol), copper (I) iodide (0.05 g, 0.3 mmol), triethylamine (10 mL), and toluene (50 mL) were combined and heated to 100 0C for 12 hours. The solution was filtered, solvent evaporated and the crude material purified on silica (25% EtOAc/hexanes) to yield a white solid. The solid material was dissolved in THF (50 mL) and 1 equivalent of TBAF was added and the solution was stirred for 1 hour at room temperature. Methylene chloride was added and the organic layer was washed 3 times with water and evaporated to yield a white solid.
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20 - 100℃; for 24h; Inert atmosphere; Sealed tube;
  • 4
  • [ 33513-42-7 ]
  • [ 57356-64-6 ]
  • [ 149806-11-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - -70℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h; 8.II To a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid.
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - 70℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h; Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water 17; 8.II To a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid.
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - -70℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h; 8.II; 4 To a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid.
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - -70℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes 8.II Part II: Preparation of 2-piperidin-1-yl-pyrimidine-5-carbaldehydeTo a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid.

  • 5
  • [ 720689-55-4 ]
  • [ 57356-64-6 ]
  • 3-cyclobutyl-7-[2-(1-piperidinyl)-5-pyrimidinyl]oxy}-2,3,4,5-tetrahydro-1H-3-benzazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-cyclobutyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ol With pyridine; sodium hydride; copper(I) bromide at 0 - 20℃; for 0.5h; Stage #2: 5-bromo-2-(piperidin-1-yl)pyrimidine for 2h; Heating / reflux; 140 Sodium hydride (60% disp. in mineral oil, 44 mg, 1.1 MMOL) was added to a stirred solution of 3-cyclobutyl-2, 3,4, 5-tetrahydro-1H-benzo [d] azepin-7-ol (E3) (200 mg, 0.92 MMOL) and copper (I) bromide (184 mg, 1.3 MMOL) in pyridine (10 ml) at 0 °C. After stirring for 0.5 hour at room temperature, 5-BROMO-2-(1-PIPERIDINYL) pyrimidine (D32) (0. 669 G, 2.8 MMOL) was added and the reaction mixture heated at reflux for 2 hours. The reaction was allowed to cool, filtered and the filtrate was concentrated in vacuo. The crude residue was dissolved with ethyl acetate and washed with water and brine. The organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Purification of the resulting residue by column chromatography eluting with a mixture of. 880 ammonia: ethanol : DICHLOROMETHANE (0.25 : 2.25 : 97.5 to 1: 9: 90) afforded the title compound (E140). MS (ES+) m/e 379 [M+H] +.
  • 6
  • [ 57356-64-6 ]
  • [ 1355063-50-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere 1.2: 0.33 h / 0 °C / Inert atmosphere 1.3: 0.17 h / 0 °C 2.1: caesium carbonate; pyridine; copper / 16 h / 120 °C 2.2: 16 h / 30 °C
  • 7
  • [ 57356-64-6 ]
  • [ 809236-47-3 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #3: With dihydrogen peroxide; acetic acid In tetrahydrofuran; hexane; water at 0℃; for 0.166667h; 10 A solution of 5-bromo-2-piperidin-1-ylpyrimidine (1.00 g, 4.15 mmol) in freshly distilled THF (5.2 mL), was purged with argon and cooled to -78° C. To the cooled reaction mixture was added drop-wise a solution of n-butyllithium in hexane (2.5 M, 1.99 mL, 4.98 mmol). The reaction mixture was stirred at -78° C. for 10 minutes and then added dropwise over 10 minutes to a solution of trimethyl borate (0.559 mL, 4.98 mmol) in THF (5.2 mL), which had been purged with argon and cooled to 0° C. The resulting reaction mixture was stirred at 0° C. for a further 20 minutes, followed by addition of acetic acid (0.356 mL, 6.22 mmol). After a further 5 minutes of stirring, a 30% aqueous solution of hydrogen peroxide (0.517 mL, 4.57 mmol) was added dropwise and stirring continued at 0° C. for 5 minutes. A saturated aqueous solution of sodium bisulfite (50 mL) was added and the mixture extracted with EtOAc. The organic extract was washed with a saturated aqueous brine solution, dried over anhydrous sodium sulfate, filtered over Celite and concentrated in vacuo. The crude material was purified using silica gel chromatography eluting with 25% EtOAC in hexane to afford the title compound (728 mg, 98%):1H NMR (400 MHz, CDCl3): δ 1.40-1.70 (br, 6H), 3.55-3.75 (br, 4H), 8.05 (d, 2H). MS m/z 180 [MH]+, 178 [M-H]- CHN Theory-C, 60.32%, H, 7.31%, N, 23.45%CHN Found-C, 60.32%; H, 7.43%; N, 23.10%.
  • 8
  • [ 57356-64-6 ]
  • [ 1196156-92-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 24 h / 20 - 100 °C / Inert atmosphere; Sealed tube 2: potassium carbonate / 0.5 h / 20 °C / Inert atmosphere
  • 9
  • [ 57356-64-6 ]
  • [ 1407999-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 24 h / 20 - 100 °C / Inert atmosphere; Sealed tube 2: potassium carbonate / 0.5 h / 20 °C / Inert atmosphere 3: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 90 °C
  • 10
  • [ 557-21-1 ]
  • [ 57356-64-6 ]
  • 2-(piperidin-1-yl)pyrimidine-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In tetrahydrofuran; water at 40℃; for 18h; Inert atmosphere;
96% With C12H10N(1-)*CH3O3S(1-)*Pd(2+)*C39H32OP2 In tetrahydrofuran; water at 65℃; for 5h; Micellar solution;
  • 11
  • [ 57356-64-6 ]
  • [ 22539-51-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium methanolate / 1,2-dimethoxyethane / 0.17 h / 30 °C 1.2: 1 h / 30 °C 2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 100 °C
  • 12
  • [ 185990-03-8 ]
  • [ 57356-64-6 ]
  • [ 1015242-08-6 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Stage #2: 5-bromo-2-(piperidin-1-yl)pyrimidine In 1,2-dimethoxyethane at 30℃; for 1h;
  • 13
  • [ 1257628-83-3 ]
  • [ 57356-64-6 ]
  • [ 1257628-60-6 ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; Sealed tube; Inert atmosphere; 3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide General procedure: A mixture of 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide 8 (192 mg, 0.5 mmol), N-cyclopropyl-5-bromopyrimidin-2-amine9 (107 mg,0.5 mmol), Cu(I)iodide (19mg, 0.1mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol), PCy3 (2.8 mg,0.01 mmol), DIPEA (193 mg, 1.5 mmol), and DMF (3 mL) were added to a sealed tube. The tube was evacuated and backfilled with argon (3 cycles). After stirring at 60°C for 12 h, the reaction mixture was filtered and washed three times with EtOAc. The solvent was removed under vacuum and the resultant crude material was purified by column chromatography to give the title compound 4e (193 mg, yield 75%).
  • 14
  • [ 5459-93-8 ]
  • [ 57356-64-6 ]
  • N-cyclohexyl-N-ethyl-2-(piperidin-1-yl)pyrimidin-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With cyclopentyl methyl ether; methanesulfonato(2-bis(3,5-di(trifluoromethyl)phenylphosphino)-3,6-dimethoxy-2',6'-bis(dimethylamino)-1,1'-biphenyl)(2'-methylamino-1,1'-biphenyl-2-yl)palladium(II); 2'-(bis(3,5-bis(trifluoromethyl)phenyl)phosphanyl)-3',6'-dimethoxy-N2,N2,N6,N6-tetramethyl-[1,1'-biphenyl]-2,6-diamine; sodium t-butanolate at 60℃; for 16h; Inert atmosphere;
  • 15
  • [ 57356-64-6 ]
  • 4-phenyl-2-(2-(piperidin-1-yl)pyrimidin-5-yl)butanenitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; N,N`-dimethylethylenediamine; sodium iodide / 1,3-dioxane / 24 h / 110 °C / Inert atmosphere 2: (S)-4-benzyl-2-(2-(bis(4-methoxy-3,5-dimethylphenyl)phosphanyl)phenyl)-4,5-dihydrooxazole; manganese; chloro-trimethyl-silane; (1,2-dimethoxyethane)dichloronickel(II) / 1,4-dioxane / 16 h / 20 °C / Inert atmosphere; Sealed tube
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