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[ CAS No. 830346-49-1 ] {[proInfo.proName]}

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Chemical Structure| 830346-49-1
Chemical Structure| 830346-49-1
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Product Details of [ 830346-49-1 ]

CAS No. :830346-49-1 MDL No. :
Formula : C26H26BrF4N3O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 600.40 Pubchem ID :-
Synonyms :

Safety of [ 830346-49-1 ]

Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

Application In Synthesis of [ 830346-49-1 ]

* 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 [ 830346-49-1 ]

[ 830346-49-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 830346-48-0 ]
  • (R)-N-(tert-butoxycarbonyl)phenylglycinol [ No CAS ]
  • [ 830346-49-1 ]
YieldReaction ConditionsOperation in experiment
99% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 14h; Add <strong>[830346-48-0]5-bromo-1-(2-fluoro-6-(trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione</strong> (2.2g, 5.8mmol at 25) )withTetrahydrofuran (35mL) was added to a 100mL single-necked round bottom flask, and (R)-tert-butyl (2-hydroxy-1-phenylethyl) carbamate (1.7g, 7.2mmol) andTriphenylphosphine (2.3g, 8.7mmol), then add diethyl azodicarboxylate (2.0g, 8.5mmol), continue to stir and react for 14 hours;The reaction was stopped, the product was spin-dried under reduced pressure, and separated and purified by column chromatography (petroleum ether/ethyl acetate (v/v)=3/1) to obtain the title compound as a white solid (3.42 g, 99%).
70% With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In toluene; at 5 - 20℃; To a stirred solution of 5-bromo-l-[2-fluoro-6-(trifluoromethyl)benzyl]-6- methylpyrimidine-2,4(lH,3H)-dione of Formula V (25 g) in toluene (275 ml) were added N- t-Boc-D-phenylglycinol of Formula VI (R3=OH, PG=Boc) (19.5 g) and triphenylphosphine (25.6 g) followed by slow addition of di tert-butyl azodicarboxylate in toluene solution (22.5 g in 100 ml) at 5-10C and stirred at RT for overnight. The resulting mixture was concentrated under vacuum to get 5-bromo-l-[2-fluoro-6-(trifluoromethyl) benzyl]-6- methyl-3-[2(R)-tert-butoxycarbonylamino-2-phenylethyl]-pyrimidine-2,4-(lH,3H)-dione which was crystallised in methanol: water (175 ml: 50 ml) to get pure compound of Formula II (27.5g, 70% yield).
With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; To 5-BROMO-1-[2-FLUORO-6-(TRIFLUOROMETHYL) benzyl] -6-methylpyrimidine- 2,4 (1FI, 3H)-DIONE LD (15 g, 39.4 mmol) in 225 mL of THF were added N-T-BOC-D- phenylglycinol (11.7 g, 49.2 mmol) and triphenylphosphine (15.5 g, 59.1 mmol), followed by addition of di-tert-butyl azodicarboxylate (13.6 g, 59.1 mmol). The resulting yellow solution was stirred overnight. The volatiles were evaporated and the residue was purified by silica gel with 3: 7 EtOAc/Hexane to give le as a white solid (23.6 g, 39.4 mmol). MS (CI) m/z 500.0 (MH+-Boc).
With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; To 5-BROMO-1- [2-FLUORO-6- (TRIFLUOROMETHYL) BENZYL]-6-METHYLPYRIMIDINE- 2,4 (1H, 3H)-DIONE LD (15 g, 39.4 mmol) in 225 mL of THF were added N-T-BOC-D- phenylglycinol (11.7 g, 49.2 mmol) and triphenylphosphine (15.5 g, 59.1 mmol), followed by addition of di-tert-butyl azodicarboxylate (13.6 g, 59.1 mmol). The resulting yellow solution was stirred overnight. The volatiles were evaporated and the residue was purified by silica gel with 3: 7 EtOAc/Hexane to give le as a white solid (23.6 g, 39.4 mmol). MS (CI) M/Z 500.0 (MH+-Boc).
With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 5 - 25℃; for 2.2h; 29.95 g of intermediate N-6, 26.86 g of D-BOC-phenylglycinol, 30.92 g of triphenylphosphine and 299 mL of tetrahydrofuran are loaded in that order into a round- bottom flask. It is cooled to 5 C and a solution of di-tert-butyl azodicarboxylate (27.19 g) dissolved in 150 mL of tetrahydrofuran is dripped in about 40 minutes. The system is brought to 25 C and kept in agitation for 1.5 hours. (0088) At the end of the reaction (HPLC control) the solvent is removed by distillation at reduced pressure at 45 C. The residue is added with 377 mL of isopropyl acetate and kept in agitation at 5-10 C for 1 hour. The suspension is filtered by washing the solid with 20 mL of isopropyl acetate. (0089) The liquid phase obtained by filtration is concentrated at reduced pressure at 45 C until a yellow oil is obtained that is reacted as such in the subsequent reaction. (0090) The compound N-6, used as a starting reactant of the method, has the appearance of a white solid; its purity, determined with HPLC, is 99%. 1H-NMK (400MHz, DMSO-d6): 511.91 (s, 1H); 7.66 (d, 1H, J = 7.6 Hz); 7.59-7.51 (m, 2H); 5.34 (s, 2H); 2.46 (s, 3H); (0091) A sample of the intermediate N-5 obtained in the test of the example, purified exclusively for analytical purposes, is analysed and identified through 1H-NMR and mass spectroscopy. 1H-NMK (400MHZ, DMSO-d6): 7.66 (d, 1H, J = 7.6 Hz); 7.61-7.48 (m, 2H); 7.36-7,21 (m, 5H); 5.35 (dd, 2H, J = 22,0/17.0 Hz); 4.93-4.88 (m, 1H); 4.10-3.99 (m, 2H); 2.53 (s, 3H); 1.35 (s, 9H).

  • 2
  • [ 830346-49-1 ]
  • [ 352303-67-4 ]
  • [ 830346-51-5 ]
YieldReaction ConditionsOperation in experiment
83% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; To 5-bromo-1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methyl-3-[2 (R) - tert-butoxycarbonylamino-2-phenylethyl] -pyrimidine-2, 4 (1H, 3H)-dione le (15 g, 25 mmol) in 30 mL/90 mL of H2O/DIOXANE in a pressure tube were added 2-fluoro-3- methoxyphenylboronic acid (4.25 g, 25 mmol) and sodium carbonate (15.75 g, 150 mmol). N2 gas was bubbled through for 10 min. Tetrakis (triphenylphosphine) palladium (2.9 g, 2.5 mmol) was added, the tube was sealed and the resulting mixture was heated at 90 C overnight. After cooling to ambient temperature, the precipitate was removed by filtration. The volatiles were removed by evaporation and the residue was partitioned between EtOAc/sat. NAHC03. The organic solvent was evaporated and the residue was chromatographed with 2: 3 EtOAc/Hexane to give 13.4 g (20.8 mmol, 83 %) yellow solid. This yellow solid (6.9 g, 10.7 mmol) was dissolved in 20 ML/20 mL CH2C12/TFA. The resulting yellow solution was stirred at room temperature for 2 hours. The volatiles were evaporated and the residue was partitioned between EtOAc/ sat. NAHC03. The organic phase was dried over NA2S04. Evaporation gave lf as a yellow oil (4.3 g, 7.9 mmol, 74%). 1H NMR (CDC13) 8 2.031 (s, 3H), 3.724-4. 586 (m, 6H), 5.32-5. 609 (m, 2H), 6.736-7. 558 (m, 11H) ; MS (CI) M/Z 546.0 (MH+). 3- [2 (R)-AMINO-2-PHENYLETHYL]-5- (2-FLUORO-3-METHOXYPHENYL)-L- [2, 6- DIFLUOROBENZYL]-6-METHYL-PYRIMIDINE-2, 4 (1H, 3I)-DIONE LF. L was made using the same procedure described in this example.
83% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; To 5-bromo-l- [2-fluoro-6- (trifluoromethyl) benzyl]-6-methyl-3- [2 (R) - tert-butoxycarbonylamino-2-phenylethyl] -pyrimidine-2, 4 (1H, 3H )-DIONE LE (15 g, 25 mmol) in 30 mL/90 mL of H2O/dioxane in a pressure tube were added 2-fluoro-3- methoxyphenylboronic acid (4.25 g, 25 mmol) and sodium carbonate (15.75 g, 150 mmol). N2 gas was bubbled through for 10 min. Tetrakis (triphenylphosphine) palladium (2.9 g, 2.5 mmol) was added, the tube was sealed and the resulting mixture was heated with stirring at 90 C overnight. After cooling to ambient temperature, the precipitate was removed by filtration. The volatiles were removed by evaporation and the residue was partitioned between EtOAc/sat. NAHC03. The organic solvent was evaporated and the residue was chromatographed with 2: 3 EtOAc/Hexane to give 13.4 g (20.8 mmol, 83 %) yellow solid. This yellow solid (6.9 g, 10.7 mmol) was dissolved in 20 mL/20 mL CH2C12/TFA. The resulting yellow solution was stirred at room temperature for 2 hours. The volatiles were evaporated and the residue was partitioned between EtOAc/ sat. NAHC03. The organic phase was dried over NA2S04. Evaporation gave If as a yellow oil (4.3 g, 7.9 mmol, 74%). 'H NMR (CDC13) 8 2.03 (s, 3H), 3.72-4. 59 (m, 6H), 5.32-5. 61 (m, 2H), 6.74-7. 56 (M, 11H) ; MS (CI) M/Z 546.0 (MH+).
83% To 5-BROMO-1- [2-FLUORO-6- (TRIFLUOROMETHYL) BENZYL]-6-METHYL-3- [2 (R) - TERT-BUTOXYCARBONYLAMINO-2-PHENYLETHYL]-PYRIMIDINE-2, 4 (1H, 3H)-DIONE 4e (15 g, 25 mmol) in 30 mL/90 mL of H2O/DIOXANE in a pressure tube were added 2-fluoro-3- methoxyphenylboronic acid (4.25 g, 25 mmol) and sodium carbonate (15.75 g, 150 mmol). N2 gas was bubbled through for 10 min. Tetrakis (triphenylphosphine) palladium (2.9 g, 2. 5 mmol) was added, the tube was sealed and the resulting mixture was heated at 90 oC overnight. After cooling to ambient temperature, the precipitate was removed by filtration. The volatiles were removed by evaporation and the residue was partitioned between EtOAc/sat. NAHC03. The organic solvent was evaporated and the residue was chromatographed with 2: 3 EtOAc/Hexane to give 13.4 g (20.8 mmol, 83 %) yellow solid
67% With palladium diacetate; potassium carbonate; XPhos; In toluene; at 110℃; for 16h;Inert atmosphere; The (R)-tert-butyl (2-(5-bromo-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo-2, 3-dihydropyrimidine-1(6H)-yl)-1-phenylethyl)carbamate (5.1g, 16.7mmol),(2-Fluoro-3-methoxy-phenyl)boronic acid (4.25g, 25.0mmol), potassium carbonate (6.98g, 50.0mmol),2-Dicyclohexylphosphorus-2',4',6'-triisopropylbiphenyl (810mg, 1.67mmol), palladium acetate (190mg, 0.83mmol) andToluene (160mL) was added to a 250mL single-necked round bottom flask, and reacted at 110C for 16 hours under nitrogen protection;The reaction was stopped, after cooling to room temperature, filtered, and the filtrate was spin-dried under reduced pressure.Separation and purification by column chromatography (petroleum ether/ethyl acetate (v/v)=4/1) gave the title compound as a white solid (7.25 g, 67%).
With potassium phosphate; (2?dicyclohexylphosphino?2?,4?,6??triisopropyl?1,1??biphenyl)[2?(2??methylamino?1,1??biphenyl)]palladium(II) methanesulfonate; In 1,4-dioxane; water; at 70℃; for 3.5h; 6 g of tert-butyl (R)-(2-(5-bromo-3-(2-fluoro-6-(trifluoromethyl)benzyl)-4-methyl-2,6-dioxo- 3,6-dihydropyrimidin-l(2H)-yl)-l-phenylethyl)carbamate and 2.2 g of 2-fluoro-3- methoxyphenyl)boronic acid were dissolved in 80 ml of dioxane. To the mixture a solution of 6.36 g of potassium phosphate tribasic in 20 ml of water was added. Obtained clear solution was degassed for 10 min at room temperature. Then, 8.6 mg of Pd-Xphos-G4 was added. The solution was stirred at 70 C for 3.5 hours. Reaction mixture was cooled down to approx 45 C and approx 50 ml of the solvent was removed by evaporation. The residue was diluted with 70 ml of ethyl acetate and 70 ml of saturated aqueous solution of NaHCCfi. The phases were separated and the aqueous phase was extracted once more with 70 ml of ethyl acetate. The combined organic extracts were dried over MgS04, filtered and concentrated to provide 5.9 g (91% of theoretical yield) of compound (7) (purity 91% HPLC IN).

  • 3
  • [ 476493-27-3 ]
  • [ 830346-49-1 ]
  • [ 1308380-86-0 ]
YieldReaction ConditionsOperation in experiment
33% In acetonitrile at 120℃; for 3h; Microwave irradiation; 22.A Step A. {(R)-2-[5-(4-benzyl-3-hydroxymethyl-piperazin-1-yl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (1-Benzyl-piperazin-2-yl)-methanol (200 mg, 0.97 mmol), {(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (50 mg, 0.083 mmol), and acetonitrile (1 mL) were placed in a microwave vessel and stirred at 120° C. for 3 hrs with microwave irradiation. After concentration of the solution, the residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 1/1/1) and dried in a vacuum to afford 20 mg of a colorless oil (yield 33%) . 1H NMR (300 MHz, CDCl3) δ 1.37 (9H, s), 2.23 (1H, m), 2.34 (3H, s), 2.41-2.66 (2H, m), 2.85 (1H, m), 3.16 (1H, m), 3.49 (1H, m), 3.72 (1H, m), 3.93-4.15 (3H, m), 4.21 (1H, m), 5.03 (1H, m), 5.42 (2H, dd), 5.74 (1H, m), 7.21 (2H, m), 7.18-7.26 (10H, m), 7.54 (1H, d)
In acetonitrile at 120℃; for 3h; microwave irradiation; 22.A (1-Benzyl-piperazin-2-yl)-methanol (200 mg, 0.97 mmol), {(R)-2-[5-bromo-3-(2-fluoro-6-trifluoromethylbenzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (50 mg, 0.083 mmol), and acetonitrile (1 mL) were placed in a microwave vessel and stirred at 120°C for 3 hrs with microwave irradiation. After concentration of the solution, the residue was purified using silica gel chromatography(eluent: hexane/ethyl acetate/dichloromethane, 1/1/1) and dried in a vacuum to afford 20 mg of a colorless oil (yield 330) [Show Image] 1H NMR (300MHz, CDCl3) δ 1.37(9H, s), 2.23(1H, m), 2.34(3H, s), 2.41-2.66(2H, m), 2.85(1H, m), 3.16(1H, m), 3.49(1H, m), 3.72(1H, m), 3.93-4.15(3H, m), 4.21(1H, m), 5.03(1H, m), 5.42(2H, dd), 5.74(1H, m), 7.21(2H, m), 7.18- 7.26(10H, m), 7.54(1H, d)
  • 4
  • [ 830346-49-1 ]
  • [ 352303-67-4 ]
  • [ 830346-51-5 ]
  • 2,2'-difluoro-3,3'-dimethoxy-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide; In acetone; for 5h;Inert atmosphere; Reflux; 12 g of compound VI and 9.53 g of <strong>[352303-67-4]2-fluoro-3-methoxybenzeneboronic acid</strong> were added to the reaction flask.4.48g sodium hydroxide, 3.24g tetrakistriphenylphosphine palladium and 200mL acetone, nitrogen protection,Heat to reflux, after 5 hours, Add 3.32 g of acetic acid and continue to reflux for 1 hour. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. 0.34 g of a white solid was obtained.Its structural identification data is as follows:
  • 5
  • [ 830346-47-9 ]
  • [ 830346-49-1 ]
  • 6
  • [ 830346-46-8 ]
  • [ 830346-49-1 ]
  • 7
  • [ 830346-48-0 ]
  • [ 102089-75-8 ]
  • [ 830346-49-1 ]
YieldReaction ConditionsOperation in experiment
90 g With tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 25 - 60℃; for 4h; Toluene (600 ml), water (300.0 ml) were added to 5-bromo-1-(2-fluoro-6- (trifluoromethyl)benzyl)-6-methylpyrimidine-2,4(1H,3H)-dione (100 gms) at 25-30C. Potassium carbonate (92 gms), tetrabutylammonium bromide (42 gms) and the compound of example-4 were added to the above reaction mixture at 25-30C. Heated the reaction mixture to 55-60C and stirred for 4 hrs at same temperature. Separated the organic layer and washed the organic layer with water. Distilled off the solvent from the organic layer. Dissolved the obtained crude in ethyl acetate and added to pre-cooled n-heptane, stirred for about 2 hrs. Filtered the precipitated solid and added to ethyl acetate and methanol followed by heating the reaction mixture to 55-60C and stirred for about 1 hr at same temperature. Cooled the reaction mixture to 25-30C and stirred for about 1 hr at same temperature. Filtered the obtained solid, washed with the mixture of ethylene glycol and methanol followed by water and then dried to get the title compound. (0088) (Yield: 90 gms, purity: 99.29% by HPLC, Impurity-la: 0.28%, Impurity-2a: 0.20%, Impurity- 3a: Not detected).
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