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[ CAS No. 886366-20-7 ]

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Chemical Structure| 886366-20-7
Chemical Structure| 886366-20-7
Structure of 886366-20-7 * Storage: {[proInfo.prStorage]}

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Product Details of [ 886366-20-7 ]

CAS No. :886366-20-7 MDL No. :MFCD03646032
Formula : C7H8BrN3 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :214.06 g/mol Pubchem ID :-
Synonyms :

Safety of [ 886366-20-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 886366-20-7 ]

  • Downstream synthetic route of [ 886366-20-7 ]

[ 886366-20-7 ] Synthesis Path-Downstream   1~20

YieldReaction ConditionsOperation in experiment
96%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h; Synthesis of (5-bromo-pyrimidin-2-yl)-tert-butyl-amine General procedure: Synthesis of (5-bromo-pyrimidin-2-yl)-tert-butyl-amine To a vial is added R-12 (200 mg, 1.13 mmol) in DMF (5 ml), followed by the addition of K2CO3 (312 mg, 2.26 mmol) and isopropylamine (134 mg, 2.27 mmol). The reaction mixture is stirred at 70° C. for 3 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water, brine, dried under anhy. Na2SO4, filtered and concentrated to afford the title intermediate (221 mg); m/z 216.0/218.0 [M/M+2H].
  • 2
  • [ 32779-36-5 ]
  • [ 765-30-0 ]
  • [ 886366-20-7 ]
YieldReaction ConditionsOperation in experiment
96% In tetrahydrofuran at 65℃; for 5h; Sealed tube;
95% With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 80℃; for 19h; microwave reaction; 64.1 To a 20 mL microwave reaction vial were added 5-bromo-2- chloropyrimidine (500 mg, 2.59 mmol), z-PrOH (7 mL), DIEA (0.90 mL, 5.45 mmol), and cyclopropylamine (0.20 mL, 2.85 mmol). The vial was sealed and heated to 80°C for 19 h, then the mixture was cooled, Celite was added and the mixture was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography, eluting with 0-100% EtOAc in hexanes, to afford (5- bromopyrimidin-2-yl)cyclopropylamine (522.2 mg, 95%) as a solid. LC-MS (ESI) w/z 214, 216 (M +H)+.
95% In ethanol at 80℃; for 3h; 1.4 Step 4. 5-bromo-N-cyclopropylpyrimidin-2-amine In a pressure tube with one end sealed, add 193 mg 5-bromo-2-chloropyrimidine (1.0 mmol) and 285 mg cyclopropylamine (5.0 mmol) in 3.0 mL ethanol, and the mixture is heated to 80 °Cand stirred for 3 h. The reaction mixture was cooled to room temperature, and 203 mg solid product was collected by filitration for direct useyield: 95%).MS (ESI), m/z: 215 (M+ + H+).
95% In ethanol at 80℃; for 3h; Sealed tube; 1.4 Step 4. 5-bromo-N-cyclopropylpyrimidin-2-amine In a pressure tube with one end sealed, add 193 mg 5-bromo-2-chloropyrimidine (1.0 mmol) and 285 mg cyclopropylamine (5.0 mmol) in 3.0 mL ethanol, and the mixture is heated to 80° C. and stirred for 3 h. The reaction mixture was cooled to room temperature, and 203 mg solid product was collected by filtration for direct use yield: 95%). MS (ESI), m/z: 215 (M++H+).
95.5% In tetrahydrofuran at 56℃; for 5h; Sealed tube; 5.1 Step 1. Step 1. 5-Bromo-N-cyclopropylpyrimidin-2-amine A solution of 5-bromo-2-chloropyrimidine (3.87 g, 20 mmol) and cyclopropylamine (5.7 g, 0.1 mol) in 20 mL THF was heated at 65° C. for 5 hrs in a sealed tube. The mixture was evaporated in vacuo, to the residue ethanol was added, after filtration, the cake was washed with ethanol to give 4.07 g product as a colorless solid (95.5%). 1H NMR (300 MHz, CDCl3) δ: 8.32 (2H, s), 5.58 (1H, brs), 2.72 (1H, brs), 0.82-0.84 (2H, m), 0.54 (2H, brs). LCMS: m/z [M+H]+ 214.0011.
86% In ethanol at 20 - 80℃; 322.3 Step 3:
5-bromo-N-cyclopropyl-pyrimidin-2-amine To a solution of 5-bromo-2-chloro-pyrimidine (2 g, 10.3 mmol) in ethanol (20 mL) at room temperature was added cyclopropylamine (1.18 g, 20.7 mmol). The resulting mixture was stirred at 80° C. overnight. The reaction mixture was diluted with EtOAc and washed with a saturated NaHCO3 aqueous solution. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the title compound (1.9 g, 86% yield) as a white solid. LCMS (M+H)+ 214.
In ethanol at 80℃; Sealed tube;
1.3 g With N-ethyl-N,N-diisopropylamine In isopropyl alcohol 5.1 Step 1:5-bromo-N-cyclopropyl-pyrimidin-2-amine synthesis The 1.0g5-bromo -2 chloro pyrimidine dissolved in 15 ml isopropanol, then the 0.35g and cyclopropylamine 1.34gN, N-diisopropyl ethylamine is added to solution in, N 2 protection, heating reflow, precipitating a large amount of white solid. turns on lathe does the solvent, extraction, anhydrous sodium sulfate for drying, filtering, turns on lathe does 1.5g white solid, recrystallization ethyl acetate, to obtain 1.3g white needle-like solid.

  • 3
  • [ 886366-20-7 ]
  • [ 1314640-57-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 80 °C 2: methanol; potassium carbonate / tetrahydrofuran
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 / methanol / 0.5 h / 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: dichloromethane / 1 h / 20 °C
Multi-step reaction with 2 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 60 °C
Multi-step reaction with 2 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C

  • 4
  • [ 886366-20-7 ]
  • [ 1257628-62-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 80 °C 2: methanol; potassium carbonate / tetrahydrofuran 3: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 80 °C
  • 5
  • [ 886366-20-7 ]
  • [ 1066-54-2 ]
  • N-cyclopropyl-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 80℃;
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20 - 100℃; for 24h; Inert atmosphere; Sealed tube;
1.1 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere; 5.2 5-Bromo-N-cyclopropylpyrimidin-2-amine (1.06 g, 5 mmol), trimethylsilylacetylene (2.5 g, 25 mmol), Pd(PPh3)4 (289 mg, 0.25 mmol) and CuI (71 mg, 0.375 mmol) were placed in a two neck flask with a rubber plug. The mixture underwent 3 cycles of vacuum and filling with Ar2, a solution of DIPEA (968 mg, 0.45 mmol) and DMF (10 mL) was injected to the flask. The mixture was stirred at 80° C. for 15 hrs, and then was poured into 50 mL water, extracted with EtOAc (30 mL×3), organic layer was washed with brine, dried with Na2SO4, filtered, and the filtrate was evaporated in vacuo. The residue was purified by chromatography on silica gel (PE/EtOAc 82:18 to 64:36) to give 1.1 g N-cyclopropyl-5-(2-(trimethylsilyl)ethynyl)pyrimidin-2-amine. This compound was dissolved in 20 mL CH2Cl2, a solution of TBAF (1.3 g, 5 mmol) in 10 mL CH2Cl2 was added into the above solution. The mixture was stirred at rt for 1 h, evaporated in vacuo. The residue was purified by chromatography on silica gel (PE/EtOAc 82:18 to 64:36) to give 0.55 g product as a pale yellow solid (72.8%). 1H NMR (300 MHz, CDCl3) δ: 8.43 (2H, s), 5.77 (1H, brs), 3.18 (1H, s), 2.76-2.81 (1H, m), 0.82-0.87 (2H, m), 0.54-0.59 (2H, m). LCMS: m/z [M+H]+ 160.0863.
1.1 g With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere; 5.2 Steps 2:N-cyclopropyl-5 - ((trimethyl silyl) ethynyl) pyrimidine-2-synthesis of amines The 1.0g5-bromo-N-cyclopropyl-pyrimidin-2-amine used 20mlDMF dissolved, then the 0.92g trimethyl silyl acetylene, 0.164gPd (dppf) 2 Cl 2, 0.09g cuprous iodide and 1.51gN, N-diisopropyl ethylamine is added to the solution, the air, plus N 2 protection, heating to 70 °C react about 2h is finished. Extraction, anhydrous sodium sulfate for drying, filtering, turns on lathe does 1.4g crude product, then purified by silica gel column chromatography, using ethyl acetate: petroleum ether = 1:20 elution, shall be 1.1g title compound.
1.1 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;

  • 6
  • [ 886366-20-7 ]
  • [ 1407999-90-9 ]
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 / methanol / 0.5 h / 20 °C / Inert atmosphere 3: copper(II) sulfate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 90 °C
  • 7
  • [ 886366-20-7 ]
  • [ 1257628-83-3 ]
  • [ 1257628-56-0 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 12h; Inert atmosphere; 1.5 Step 5. 3-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (D747) In a pressure tube with one end sealed, add 192 mg step 3 product, 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl) phenyl)benzamide (0.5 mmol), 107 mg Step 4 product, 5-bromo-N-cyclopropylpyrimidin-2-amine (0.5 mmol), 19 mg CuI (0.1 mmol), 2.2 mg Pd(OAc)2 (0.01 mmol), 2.8 mg PCy3(0.01 mmol) 3.0 mL DMF, 193 mg DIPEA (1.5 mmol), after nitrogen replacement, the solution is heated to 60 °C for 12 h. After cooling to room temperature, the solid is filtered off by 2 cm silical gel column and washed by ethyl acetate for three times, and the solution was concentrated by vacuum evaporation for 193 mg desired product (75%).; 1HNMR (400 MHz, d-DMSO), δ ppm 10.69 (s, 1H), 8.54 (br, 2H), 8.29 (s, 1H), 8.21 (s, 1H), 8.16 (m, 2 H), 7.93 (m, 2H), 7.73 (s, 1H), 7.52 (m, 2H), 2.77 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 0.71 (m, 2H), 0.53 (m, 2H). MS (ESI), m/z: 517 (M++ H+).
75% With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 12h; Sealed tube; Inert atmosphere; 1.5 Step 5. 3-(2-(2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (D747) In a pressure tube with one end sealed, add 192 mg step 3 product, 3-ethynyl-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.5 mmol), 107 mg Step 4 product, 5-bromo-N-cyclopropylpyrimidin-2-amine (0.5 mmol), 19 mg CuI (0.1 mmol), 2.2 mg Pd(OAc)2 (0.01 mmol), 2.8 mg PCy3 (0.01 mmol) 3.0 mL DMF, 193 mg DIPEA (1.5 mmol), after nitrogen replacement, the solution is heated to 60° C. for 12 h. After cooling to room temperature, the solid is filtered off by 2 cm silical gel column and washed by ethyl acetate for three times, and the solution was concentrated by vacuum evaporation for 193 mg desired product (75%). 1HNMR (400 MHz, d-DMSO), δ ppm 10.69 (s, 1H), 8.54 (br, 2H), 8.29 (s, 1H), 8.21 (s, 1H), 8.16 (m, 2H), 7.93 (m, 2H), 7.73 (s, 1H), 7.52 (m, 2H), 2.77 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 0.71 (m, 2H), 0.53 (m, 2H). MS (ESI), m/z: 517 (M++H+).
75% With copper(l) iodide; palladium diacetate; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine In N,N-dimethyl-formamide at 60℃; for 12h; 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%).1HNMR (400 MHz, d-DMSO), δ ppm 10.69 (s, 1H), 8.54(br, 2H), 8.29 (s, 1H), 8.21 (s, 1H), 8.16 (m, 2 H), 7.93 (m, 2H), 7.73(s, 1H), 7.52 (m, 2H), 2.77 (m, 1H), 2.53 (s, 3H), 2.18 (s, 3H), 0.71 (m, 2H), 0.53(m, 2H). MS (ESI), m/z: 517 (M + H). HRMS (EI): calcd forC28H23F3N6O: 517.1885 [M+H];
  • 8
  • [ 886366-20-7 ]
  • [ 1581701-29-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 12 h / 100 °C 2: lithium hydroxide; water / tetrahydrofuran; methanol / 3 h / 20 °C 3: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 12 h / 20 °C
  • 9
  • [ 886366-20-7 ]
  • [ 1242458-50-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / N,N-dimethyl-formamide / 12 h / 100 °C 2: lithium hydroxide; water / tetrahydrofuran; methanol / 3 h / 20 °C
  • 10
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 886366-20-7 ]
  • [ 1581701-22-5 ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 12h;
  • 11
  • [ 886366-20-7 ]
  • (R)-N-(3 ((2-(cyclopropylamine)pyrimidin-5-yl)ethynyl)-4-methylphenyl)-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-indene-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 60 °C 3: palladium diacetate; triphenylphosphine; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 80 °C
  • 12
  • [ 886366-20-7 ]
  • (S)-N-(3 ((2-(cyclopropylamine)pyrimidin-5-yl)ethynyl)-4-methylphenyl)-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere 2: potassium carbonate / methanol / 2 h / 60 °C 3: palladium diacetate; triphenylphosphine; copper(l) iodide; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6 h / 80 °C
  • 13
  • [ 886366-20-7 ]
  • tert-butyl 2-(3-acetyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)acetate [ No CAS ]
  • tert-butyl 2-(3-acetyl-5-(2-(cyclopropylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 5h; 6.1 Step 1: tert-Butyl 2-(3-acetyl-5-(2-(cyclopropylamino)pyrimidin-5-yl)-1H-indazol-1-yl)acetate (S3) To a solution of 5-bromo-N-cyclopropylpyrimidin-2-amine (S2, 1 equiv) in DMF/H2O (9:1, 10 vol) was added compound S1 (1 equiv), K2CO3(2 equiv), and tetrakis(triphenylphosphine)palladium (0.1 equiv). The reaction mixture was stirred at 90° C. for 5 h and then concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel to give compound S3.
  • 14
  • [ 886366-20-7 ]
  • 2-chloro-6-[4-[4-[2-(cyclopropylamino)pyrimidin-5-yl]-1-methyl-6-oxo-3-pyridyl]pyrazol-1-yl]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed tube 2: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; 1,4-dioxane / 2.5 h / 80 °C / Inert atmosphere; Sealed tube
  • 15
  • [ 886366-20-7 ]
  • [ 73183-34-3 ]
  • [ 1218789-33-3 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; Sealed tube; 322.4 Step 4:
N-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine A mixture of 5-bromo-N-cyclopropyl-pyrimidin-2-amine (600 mg, 2.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.1 g, 4.2 mmol), potassium acetate (550 mg, 5.6 mmol) and PdCl2(PPh3)2(393 mg, 0.56 mmol) in 1,4-dioxane (20 mL) under a nitrogen atmosphere was stirred overnight at 80° C. in a sealed tube. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography to afford the title compound as a yellow solid. LCMS (M+H)+ 180 (M-pinacol).
  • 16
  • [ 886366-20-7 ]
  • [ 1542265-14-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere
  • 17
  • [ 886366-20-7 ]
  • [ 1542265-19-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere
  • 18
  • [ 886366-20-7 ]
  • [ 1542265-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere
  • 19
  • [ 886366-20-7 ]
  • 3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-N-(3,3-difluoro-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere
  • 20
  • [ 886366-20-7 ]
  • (S)-3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-N-(3,3-difluoro-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl)-4-methylbenzamide [ No CAS ]
  • (R)-3-((2-(cyclopropylamino)pyrimidin-5-yl)ethynyl)-N-(3,3-difluoro-1-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-5-yl)-4-methylbenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / dichloromethane / 1 h / 20 °C 3: copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere 4: carbon dioxide; diethylamine / ethanol / Resolution of racemate
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Amines

Chemical Structure| 77476-95-0

[ 77476-95-0 ]

(5-Bromopyrimidin-2-yl)isopropylamine

Similarity: 0.93

Chemical Structure| 1187385-92-7

[ 1187385-92-7 ]

5-Bromo-N-propylpyrimidin-2-amine

Similarity: 0.93

Chemical Structure| 947534-33-0

[ 947534-33-0 ]

5-Bromo-N-cyclobutylpyrimidin-2-amine

Similarity: 0.89

Chemical Structure| 14001-71-9

[ 14001-71-9 ]

5-Bromo-N-butylpyrimidin-2-amine

Similarity: 0.89

Chemical Structure| 14001-72-0

[ 14001-72-0 ]

5-Bromo-N-(tert-butyl)pyrimidin-2-amine

Similarity: 0.89

Related Parent Nucleus of
[ 886366-20-7 ]

Pyrimidines

Chemical Structure| 77476-95-0

[ 77476-95-0 ]

(5-Bromopyrimidin-2-yl)isopropylamine

Similarity: 0.93

Chemical Structure| 1187385-92-7

[ 1187385-92-7 ]

5-Bromo-N-propylpyrimidin-2-amine

Similarity: 0.93

Chemical Structure| 947534-33-0

[ 947534-33-0 ]

5-Bromo-N-cyclobutylpyrimidin-2-amine

Similarity: 0.89

Chemical Structure| 14001-71-9

[ 14001-71-9 ]

5-Bromo-N-butylpyrimidin-2-amine

Similarity: 0.89

Chemical Structure| 14001-72-0

[ 14001-72-0 ]

5-Bromo-N-(tert-butyl)pyrimidin-2-amine

Similarity: 0.89