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[ CAS No. 1610705-51-5 ]

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Chemical Structure| 1610705-51-5
Chemical Structure| 1610705-51-5
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CAS No. :1610705-51-5 MDL No. :MFCD16618882
Formula : C12H17BN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :264.09 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1610705-51-5 ]

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 [ 1610705-51-5 ]

  • Downstream synthetic route of [ 1610705-51-5 ]

[ 1610705-51-5 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1610705-45-7 ]
  • [ 1610705-51-5 ]
  • [ 1610705-50-4 ]
YieldReaction ConditionsOperation in experiment
With dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); cesium fluoride In methanol; 1,2-dimethoxyethane at 110℃; for 3h; Microwave irradiation; Inert atmosphere; 4G.1 Step 1: Preparation of (S)-methyl 5-(6-(l-(cyclopropanecarbonyl)pyrrolidin-3-ylamino)-9- ethyl-9H-purin-8-yl)pyrimidine-2-carboxylate. To a solution of Intermediate VI (500 mg, 1.2 mmol) in ethylene glycol dimethyl ether (20 mL) and methanol (5 mL) were added methyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyrimidine-2-carboxylate (930 mg, 3.5 mmol) (Source: WO2007/84786 Al), bis(di-tert- butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) ((A-phos)2PdCl2 ) (84 mg, 0.12 mmol) and cesium fluoride (720 mg, 4.8 mmol). The resulting mixture was stirred in a microwave reactor (50 Watt) for 3 h at 1 10°C under a nitrogen atmosphere. The resulting mixture was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography (eluting with 1-2% methanol in dichloromethane) to afford (S)-methyl 5-(6-(l-(cyclopropanecarbonyl)pyrrolidin-3-ylamino)-9-ethyl-9H-purin-8-yl)pyrimidine-2- carboxylate. MS (ESI) calc'd for (C2iH25N803) [M+H]+, 437; found, 437
  • 2
  • [ 1610705-51-5 ]
  • trifluoromethanesulfonic acid 6-[(1S,8R)-5-(2,6-difluoro-phenyl)-11,11-dimethyl-3,4-diaza-tricyclo[6.2.1.02,7]undeca-2(7),3,5-trien-1-yl]-pyridin-2-yl ester [ No CAS ]
  • C28H23F2N5O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate In 1,4-dioxane at 20 - 90℃; for 20h; 34 Example 34: 5-(6-((5R,8S)-3-(2,6-difluorophenyl)-9,9-dimethyl-6,7-dihydro-5,8-methanocinnolin-8(5H)- yl)pyridin-2-yl)pyrimidine-2-carboxylic acid: To a solution of 6-((5R,8S)-3-(2,6-difluorophenyl)-9,9-dimethyl-6,7-dihydro-5,8- methanocinnolin-8(5H)-yl)pyridin-2-yl trifluoromethanesulfonate (Intermediate B, 125 mg, 0.244 mmol) in dioxane (1.6 mL) was added methyl 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2- carboxylate (101 mg, 0.367 mmol), potassium phosphate tribasic (145 mg, 0.611 mmol) and [(2-Di-tert- butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate (14 mg, 0.017 mmol). The reaction mixture was stirred at 90 °C for 4 h. The mixture was cooled to room temperature and [(2-Di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2- (2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate (14 mg, 0.017 mmol) was added, after which the reaction mixture was stirred at 90 °C for 16 h. The mixture was cooled to room temperature and an aqueous solution of sodium hydroxide 1 M (0.50 mL) was added and the reaction mixture was stirred at room temperature for 1 h. To the reaction mixture was added an aqueous solution of hydrogen chloride 1 N (20 mL) and DCM (20 mL). The two phases were separated and the aqueous layer was extracted with DCM (2 X). The combined organic layers were washed with brine, dried over anh. MgSO4, filtered and concentrated in vacuo. The crude residue was purified by reverse phase chromatography (acetonitrile 5-50% / 0.1 % ammonium hydroxide in water) to give the title compound (5.5 mg,) as a beige solid.1H NMR (400 MHz, DMSO-d6) δ 9.52 (s, 2H), 8.18 (d, J = 7.8 Hz, 1H), 8.07 (t, J = 7.8 Hz, 1H), 7.84- 7.75 (m, 2H), 7.68- 7.56 (m, 1H), 7.31 (t, J = 8.1 Hz, 2H), 6.65 (s, 1H), 3.39- 3.28 (m, 2H), 2.49- 2.41 (m, 1H), 1.68- 1.55 (m, 1H), 1.33- 1.23 (m, 1H), 1.11 (s, 3H), 0.75 (s, 3H). LCMS M/Z (M+H) 486.
  • 3
  • [ 89581-38-4 ]
  • [ 73183-34-3 ]
  • [ 1610705-51-5 ]
YieldReaction ConditionsOperation in experiment
60% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃;Inert atmosphere; Under the protection of N2, PdCl2(dppf) (0.337 g, 0.461 mmol) was added to an anhydrous 1,4-dioxane (200 mL) solution of <strong>[89581-38-4]methyl 5-bromo-2-pyrimidinecarboxylate</strong> (2.00g, 9.22 mmol), bis(pinacolato)diboron (2.80 g, 11.1 mol) and anhydrous potassium acetate (2.70 g, 27.7 mol), and the resulting mixture was heated to 100C to react overnight. After cooling and concentration under reduced pressure, water and ethyl acetate were added to the residue, stirred for 15 min, and filtered through Celite filler, and the Celite filler was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a brownish black residue. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (5:1) to obtain a white solid product (1.47 g, 60%). 1H NMR (400 MHz, CDCl3) delta 9.19 (s, 2H), 4.10 (s, 3H), 1.39 (s, 12H).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 2h;Microwave irradiation; Inert atmosphere; To a mixture of <strong>[89581-38-4]methyl 5-bromopyrimidine-2-carboxylate</strong> (150.0 mg, 0.69 mmol) and 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi( 1,3 ,2-dioxaborolane) [BPinj2 (211.0 mg, 0.83 mmol) in i,4-dioxane (1.8 ml) in a MW tube equipped with a stirring bar, Pd(dppf)C12 (25.0 mg, 0.04 mmol) and potassium acetate (204.0 mg, 2.07 mmol) were added under N2 bubbling through the solvent. The resulting mixture was stirred at 100C for 2 hours. After completion of the reaction, the crude reaction mixture is filtered into a MW vial equipped with a stir bar and 5-chloro-3 -phenyl-2-(( iS)- 1 -((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6- yl)amino)propyl)quinazolin-4(3H)-one 5.2r (120.0 mg, 0.23 mmol) and 0.2 ml of water were added to it. Added [Pd-170j (7.8 mg, 0.012 pmol) and potassium phosphate (148.0 mg, 0.70 mmol) to this mixture under nitrogen atmosphere. The MW vial was sealed and heated at 100C for 2 hours. The reaction mixture was allowed to cool to room temperature, quenched with water, and then extracted 3 times with ethyl acetate. The combined organic fractions were dried over MgSO4 and then concentrated in vacuo. The remaining residue was purified by flash chromatography on silica using 0-5% MeOH/DCM to afford the coupled product methyl 5-(4-oxo-3 -phenyl-2-(( iS)- 1 -((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6- yl)amino)propyl)-3 ,4-dihydroquinazolin-5-yl)pyrimidine-2-carboxylate (135.0 mg, 0.22 mmol) 1.4b in 94% yield. LC-MS (method 1): tR = 3.12 mi mlz (M + H) = 618.3.
  • 4
  • [ 1610705-51-5 ]
  • methyl 7-(3,5-dimethylisoxazol-4-yl)-9H-pyridino[2',3':4,5]pyrrolo[2,3-d]pyrimidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; water / 70 °C / Inert atmosphere 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 2 h / 180 °C / Inert atmosphere
  • 5
  • [ 1610705-51-5 ]
  • methyl 7-(3,5-dimethylisoxazol-4-yl)-9-[phenyl(tetrahydro-2H-pyran-4-yl)methyl]-9H-pyridino[2'3':4,5]pyrrolo[2,3-d]pyrimidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; water / 70 °C / Inert atmosphere 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 2 h / 180 °C / Inert atmosphere 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 - 30 °C
  • 6
  • [ 1610705-51-5 ]
  • 2-{7-(3,5-dimethylisoxazol-4-yl)-9-[phenyl(tetrahydro-2H-pyran-4-yl)methyl]-9H-pyridino[2',3':4,5]pyrrolo[2,3-d]pyrimidin-2-yl}propan-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran; water / 70 °C / Inert atmosphere 2: 1,2-bis-(diphenylphosphino)ethane / 1,2-dichloro-benzene / 2 h / 180 °C / Inert atmosphere 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 - 30 °C 4: tetrahydrofuran; diethyl ether / 2 h / -15 - 20 °C
  • 7
  • [ 1610705-51-5 ]
  • 4-(6-chloro-5-nitropyridin-3-yl)-3,5-dimethylisoxazole [ No CAS ]
  • methyl 5-[5-(3,5-dimethylisoxazol-4-yl)-3-nitropyridin-2-yl]pyridinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; water at 70℃; Inert atmosphere; 29.B Step B: Methyl 5-[5-(3,5-dimethylisoxazol-4-yl)-3-nitropyridin-2-yl]pyrimidine-2-carboxylate Under the protection of N2, PdCl2(dppf) (0.103g, 0.14 mmol) was added to a tetrahydrofuran/water (3:1=30 mL) solution of 2-chloro-5-(3,5-dimethylisoxazol-4-yl) -3-nitropyridine (0.716 g, 2.80 mmol), methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyrimidine-2-carboxylate (1.00 g, 3.79 mmol) and anhydrous potassium phosphate (0.78 g, 3.67 mmol), and the resulting mixture was heated to 70°C to react overnight. After cooling and concentration under reduced pressure, water and ethyl acetate were added to the residue, stirred for 15 min, and filtered through Celite filler, and the Celite filler was rinsed with ethyl acetate. After the filtrate was layered, the aqueous phase was extracted with ethyl acetate once. The ethyl acetate phases were combined, washed with a saturated sodium chloride aqueous solution, dried with anhydrous sodium sulfate, and concentrated to obtain a black residue. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (3:1) to obtain methyl 5 - [5 -(3,5 -dimethylisoxazol-4-yl)-3 -nitropyridin-2-yl]pyrimidine-2-carboxylate (0.32 g, 32%). 1H NMR (400 MHz, CDCl3) δ 9.18 (s, 2H), 8.93 (d, 1H), 8.32 (d, 1H), 4.13 (s, 3H), 2.56 (s, 3H), 2.40 (s, 3H).
  • 8
  • [ 1610705-51-5 ]
  • 5-chloro-3-phenyl-2-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)quinazolin-4(3H)-one [ No CAS ]
  • methyl 5-(4-oxo-3-phenyl-2-((1S)-1-((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)amino)propyl)-3,4-dihydroquinazolin-5-yl)pyrimidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With chloro(crotyl)(2-dicyclohexylphosphino-2’,4’,6’-triisopropybiphenyl)palladium(II) In water at 100℃; for 2h; Inert atmosphere; Microwave irradiation; To a mixture of methyl 5-bromopyrimidine-2-carboxylate (150.0 mg, 0.69 mmol) and 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi( 1,3 ,2-dioxaborolane) [BPinj2 (211.0 mg, 0.83 mmol) in i,4-dioxane (1.8 ml) in a MW tube equipped with a stirring bar, Pd(dppf)C12 (25.0 mg, 0.04 mmol) and potassium acetate (204.0 mg, 2.07 mmol) were added under N2 bubbling through the solvent. The resulting mixture was stirred at 100°C for 2 hours. After completion of the reaction, the crude reaction mixture is filtered into a MW vial equipped with a stir bar and 5-chloro-3 -phenyl-2-(( iS)- 1 -((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6- yl)amino)propyl)quinazolin-4(3H)-one 5.2r (120.0 mg, 0.23 mmol) and 0.2 ml of water were added to it. Added [Pd-170j (7.8 mg, 0.012 pmol) and potassium phosphate (148.0 mg, 0.70 mmol) to this mixture under nitrogen atmosphere. The MW vial was sealed and heated at 100°C for 2 hours. The reaction mixture was allowed to cool to room temperature, quenched with water, and then extracted 3 times with ethyl acetate. The combined organic fractions were dried over MgSO4 and then concentrated in vacuo. The remaining residue was purified by flash chromatography on silica using 0-5% MeOH/DCM to afford the coupled product methyl 5-(4-oxo-3 -phenyl-2-(( iS)- 1 -((9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6- yl)amino)propyl)-3 ,4-dihydroquinazolin-5-yl)pyrimidine-2-carboxylate (135.0 mg, 0.22 mmol) 1.4b in 94% yield. LC-MS (method 1): tR = 3.12 mi mlz (M + H) = 618.3.
  • 9
  • [ 1610705-51-5 ]
  • tert-butyl N-[3-chloro-6-fluoro-4-[3-(trifluoromethyl)pyrazol-1-yl]-9H-pyrido[2,3-b]indol-8-yl]-N-ethylcarbamate [ No CAS ]
  • C28H25F4N7O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride; XPhos In 1,4-dioxane at 110℃; for 4h; Inert atmosphere;
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