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[ CAS No. 3764-01-0 ] {[proInfo.proName]}

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Chemical Structure| 3764-01-0
Chemical Structure| 3764-01-0
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Product Details of [ 3764-01-0 ]

CAS No. :3764-01-0 MDL No. :MFCD00006063
Formula : C4HCl3N2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :DPVIABCMTHHTGB-UHFFFAOYSA-N
M.W : 183.42 Pubchem ID :77378
Synonyms :

Safety of [ 3764-01-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3764-01-0 ]

* 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 [ 3764-01-0 ]

[ 3764-01-0 ] Synthesis Path-Downstream   1~19

  • 1
  • [ 3764-01-0 ]
  • [ 1004-38-2 ]
  • 2
  • [ 3764-01-0 ]
  • [ 1004-38-2 ]
  • [ 156-83-2 ]
  • 3
  • [ 3764-01-0 ]
  • [ 3833-57-6 ]
  • [ 3824-45-1 ]
  • [ 696-82-2 ]
  • 4
  • [ 3764-01-0 ]
  • [ 143-66-8 ]
  • [ 2456-81-7 ]
  • 1,1',1''-(pyrimidin-2,4,6-triyl)-tris-4-(pyrrolidin-1-yl)pyridinium tris(tetraphenylborate) [ No CAS ]
  • 5
  • [ 3764-01-0 ]
  • [ 2456-81-7 ]
  • 1,1',1''-(pyrimidin-2,4,6-triyl)-tris-4-(pyrrolidin-1-yl)pyridinium tri-iodide [ No CAS ]
  • 6
  • [ 3764-01-0 ]
  • [ 2456-81-7 ]
  • (pyrimidine-2,4,6-triyl)-1,1',1''-tris[4-(pyrrolidin-1-yl)pyridinium] trichloride [ No CAS ]
  • 7
  • [ 3764-01-0 ]
  • [ 7664-41-7 ]
  • [ 1004-38-2 ]
  • 8
  • [ 3764-01-0 ]
  • [ 78581-99-4 ]
  • [ 741290-21-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In dimethyl sulfoxide; at 40℃; for 17h; A solution OF 2, 4, 6-TRICHLOROPYRIMIDIN (4.2 gram), <strong>[78581-99-4]5,6-difluorobenzimidazole</strong> (3.6 gram) and K2CO3 (6.4 gram) in dimethyl sulfoxide (150 ml) was stirred at 40 C for 17 hours. The solution was taken up in water, and extracted three times with ethyl acetate. The ethyl acetate layers were combined, washed with brine, dried over magnesium sulfate, filtered, and the solvents were removed in vacuo. Silica gel chromatography (heptane/ethyl acetate 9/1) provided 1.2 g of the title compound.
  • 9
  • [ 3764-01-0 ]
  • [ 56367-24-9 ]
  • [ 71-36-3 ]
  • [ 898281-45-3 ]
YieldReaction ConditionsOperation in experiment
70% With N-ethyl-N,N-diisopropylamine; In ethyl acetate; 2,6-Dichloropyrimidin-4-yl-(5-isopropyl-1H-pyrazol-3-yl)-amine. A mixture of 2,4,6-trichloropyrimidine (1.8 g, 9.8 mmol), 5-isopropyl-1H-pyrazol-3-ylamine (1.25 g, 10.0 mmol), diisopropylethylamine (3 mL, 18 mmol) and 1-butanol (10 mL) was heated to 80 C. for 2 h, at which point LC/MS indicated that the reaction was complete. The solvents were removed on a rotary evaporator and the paste was treated with ethyl acetate. The organic solution was washed with water and brine and dried over magnesium sulfate. The residue was concentrated on a rotary evaporator, and the pale yellow solid that remained was purified via flash chromatography to yield the desired product (2.3 g, 70%) as an off white solid.
  • 10
  • [ 3764-01-0 ]
  • [ 870119-58-7 ]
  • 2,4,6-tris(3-(carbazol-9-yl)phenyl)pyrimidine [ No CAS ]
  • 11
  • [ 3764-01-0 ]
  • [ 1036378-83-2 ]
  • [ 1384480-21-0 ]
YieldReaction ConditionsOperation in experiment
63% With sodium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; at 80℃; for 18h;Inert atmosphere; (3b) 4,6-di([1 ,1 ':3',1 "-terphenyl]-5'-yl)-2-chloropyrimidineA 250 ml_ 3-neck round-bottomed flask equipped with magnetic stir bar, thermometer, reflux condenser and nitrogen bubbler was charged with 2,4,6-trichloropyrimidine (2.20 g, 12.0 mmol), 4,4,5,5-tetramethyl-2- [1 ,1 ':3',1 "-terphenyl]-5'-yl-1 ,3,2-dioxaborolane from step (3a) (8.56 g, 24.0 mmol), triphenylphosphine (157 mg, 0.60 mmol), 1 ,2-dimethoxyethane (80 ml_) and sodium carbonate (2 M, 24 ml_, 48.0 mmol). With stirring, the system was purged with nitrogen (with N2 flowing in from the top of condenser and bubbling into the solution through a side arm) for 20 min. Palladium acetate (67 mg, 0.3 mmol) was added and the system was purged for another 15 min. The reaction was then stirred and refluxed at 80 C (heating block) under nitrogen for 18 hour. During the time some solid was formed. After cooling to ambient temperature, more solid was formed. The solid was filtered and washed with water. The crude product was dissolved in dichloromethane (200 mL) and the solution was washed with water, brine and dried over magnesium sulfate. The solution was then passed through a short Alumina (basic) column and eluted with dichloromethane. The product containing fractions (that exhibited blue fluorescence under UV lamp) were collected. The solvent was removed by rotary evaporation and the residue was crystallized fromdichloromethane/acetonitrile to give the product as a white fibrous material (4.3 g, 63%) in 97% purity by UPLC.
  • 12
  • [ 67-56-1 ]
  • [ 3764-01-0 ]
  • [ 43212-41-5 ]
  • [ 1074-40-4 ]
  • 13
  • [ 3764-01-0 ]
  • [ 1009033-87-7 ]
  • [ 181219-01-2 ]
  • C31H21N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% <a> Synthesis of Intermediate (80- 1) Intermediate (80" l) A flask was charged with 2,4,6-trichloropyridine (732 mg, 4.0 mmol), followed by being purged with argon gas. To the flask, thereafter, dioxane (60 niL), which had been deaerated with argon gas, 4-(4-pyridyl)phenyl boronic acid pinacol ester (8.0 mmol, 2.26 g), and bis(triphenylphosphine)palladium(II) dichloride (0.3 mmol, 210 mg) were added. After bubbling the solution with argon gas, 2M K2CO3 (20 mL) was added, and the resultant was heated and stirred at 50C for 4 hours. Next, 4-4,4, 5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)pyridine (4 mmol, 820 mg) was added and the resultant was heated and stirred at 100C for 4 hours. Subsequently, the resultant was filtered with Celite, and water and chloroform were added to the filtrate to separate an organic layer. Thereafter, a water layer was extracted 5 times with chloroform. The combined organic layer was washed with saturated salt water, followed by drying with sodium sulfate to condensate the filtrate, to thereby obtain a crude product. The crude product was purified by silica-gel column chromatography (eluent: chloroform/methanol = 93/7), and the obtained solids were dispersed and washed in chloroform/hexane. The solids were collected by filtration, and the obtained solids were vacuum dried to thereby obtain an intermediate (80- 1) as pale yellow solids (the yielded amount: 1.19 g, the yield: 64% H NMR (500 MHz, CDCI3, delta) : 8.87 (dd, Ji = 4.7 Hz, J2 = 1.7 Hz, 2H), 8.75 (dd, Ji = 4.0 Hz, J2 = 1.7 Hz, 4H), 8.58 (dd, Ji = 4.7 Hz, J2 = 1.7 Hz, 2H), 8.45 (dt Ji = 8.0 Hz, J2 = 1.7 Hz, 4H), 8.21 (s, 1H), 7.88 (dd, Ji = 8.6 Hz, J2 = 1.7 Hz, 4H), 7.61 (dd, Ji = 4.7 Hz, J2 = 1.7 Hz, 4H)
61% 2, 4, 6-trichloropyrimidine (732 mg, 4.0 mmol) was placed in a flask,After substitution with argon gas,Dioxane (60 mL) degassed with argon gas,4- (4-pyridyl) phenylboronic acid pinacol ester (8.0 mmol, 2.26 g) represented by the following structural formula (28)Bis (triphenylphosphine) palladium (II) dichloride (0.3 mmol, 210 mg) was added.After bubbling the solution with argon gas,2 M K 2 CO 3 (20 mL) was added,And the mixture was heated and stirred at 50 C. for 4 hours.Then 4- (4,4,5,5-tetramethyl-1,3,2-dioxeSabololan-2-yl) pyridine(4 mmol, 820 mg) was added,And the mixture was heated and stirred at 100 C. for 4 hours.Subsequently, the contents were filtered through celite, water and chloroform were added to the filtrate to separate the organic layer,The aqueous layer was extracted with chloroform.The combined organic layer was dried over sodium sulfate and the filtrate was concentrated to give a crude product.This was purified by silica gel chromatography (developing solvent: chloroform / methanol)The solid obtained after the concentration was dried under vacuum,The target compound was obtained as a pale yellow solid (yield 1.13 g, yield 61%).
  • 14
  • [ 3764-01-0 ]
  • [ 498-63-5 ]
  • (1-(2,6-dichloropyrimidin-4-yl)pyrrolidin-2-yl)methanol [ No CAS ]
  • 15
  • [ 3764-01-0 ]
  • [ 6397-33-7 ]
  • 2,5-dichloro-N-[2-(propan-2-ylsulfanyl)phenyl]pyrimidin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.5% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 8℃; for 24h;Inert atmosphere; To a 250 ml three-necked flask was added 2,4,6-trichloropyrimidine (32.9 g, 179.4 mmol, 2.0 equiv), 2- (isopropylthio) aniline (15.0 g, 89.7 mmol, 1.0 equiv) and isopropanol 150ml), nitrogen protection. N, N-diisopropylethylamine (34.8 g, 269.1 mmol, 3.0 equiv) was added. The reaction was carried out at 80 C for 24 hours and the LC / MS was used to track the reaction.After completion of the reaction, water was added and the mixture was extracted with ethyl acetate. The organic phase was washed successively with saturated sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude product. The crude oil was added with petroleum ether to obtain 12.8 g of compound of formula 8 in a yield of 45.5%.
  • 16
  • [ 3764-01-0 ]
  • [ 1009033-87-7 ]
  • C26H17ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In toluene; at 50℃; for 5h;Inert atmosphere; In a flask, 1.83 g of 2,4,6-trichloropyrimidine, 5.65 g of the boronic acid ester shown in the above scheme (1), and 0.35 g of dichlorobis (triphenylphosphine) palladium were placed and purged with argon.100 ml of toluene and 20 ml of 2 M potassium carbonate aqueous solution were added and stirred at 50 C. for 5 hours.The reaction solution was washed with an aqueous sodium chloride solution and then purified by column chromatography to obtain a colorless solid.Yield 40%.Further, the obtained solid was stirred with triple molar amount of bromooctylphosphonic acid in the presence of DMF solvent at 90 C. for 4 hours to obtain (actual -1) as a colorless solid.Yield 60%.
  • 17
  • [ 3764-01-0 ]
  • [ 1000895-26-0 ]
  • (3-((2,6-dichloropyrimidin-4-yl)amino)-1H-pyrazol-5-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With N-ethyl-N,N-diisopropylamine; In ethanol; at 20.0℃; for 12.0h; To a mixture of 2,4,6-trichloropyrimidine (8.0 g, 43.7 mmol) and <strong>[1000895-26-0](3-amino-1H-pyrazol-5-yl)methanol</strong> (7.4 g, 65.4 mmol) in EtOH (80 mL) was added DIPEA (11.3 g, 87.2 mmol). The reaction mixture was stirred at 20 C. for 12 h and filtered to give the title intermediate (6.5 g, 57% yield) as a white solid. (m/z): [M+H]+ calcd for C8H7Cl2N5O 260.00 found 260.0.
  • 18
  • [ 389621-84-5 ]
  • [ 3764-01-0 ]
  • (4-(2,6-dichloropyrimidin-4-yl)phenyl)(morpholino)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With palladium diacetate; sodium carbonate; triphenylphosphine; In tetrahydrofuran; water; at 70℃; for 6h; To a solution of 2,4,6-trichloropyrimidine (400 mg, 2.18 mmol) in tetrahydrofuran (6.6 mL) were added palladium acetate (50 mg, 0.22 mmol), triphenylphosphine (120 mg, 0.43 mmol), <strong>[389621-84-5](4-(morpholine-4-carbonyl)phenyl)boronic acid</strong> (517 mg, 2.20 mmol) and aqueous sodium carbonate (1 M, 6.6 mL, 6.6 mmol). The mixture was heated to 70 C and stirred for 6 h. To the reaction mixture was added water (50 mL), and the mixture was extracted with EtOAc (50 mL x 3). The combined organic layers were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to dry,and the residue was purified by silica gel column chromatography (PE) to give the title compound as a white solid (371 mg, 50%).MS (ESI, pos.ion) m/z: 340.0 [M+Hfb;?H NIVIR (400 IVIFIz, CDC13) (ppm):8.16 (d, J= 8.3 Hz, 2H), 7.72 (s, 1H), 7.59 (d, J = 8.3 Hz, 2H), 3.75 (d, J = 60.6 Hz, 6H), 3.46 (s, 2H).
  • 19
  • [ 3764-01-0 ]
  • [ 145214-05-7 ]
  • 2-(2,6-dichloropyrimidin-4-yl)oxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With bis(triphenylphosphine)palladium(II) dichloride; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere; 2,4,6-Trichloropyrimidine (67 mg, 0.37 mmol) was dissolved in DMF (8 mL).Additional bis(triphenylphosphine)palladium dichloride (25 mg, 0.03 mmol)And <strong>[145214-05-7]2-(tributylstannyl)oxazole</strong> (120 mg, 0.34 mmol),The resulting mixture was heated to 90 C under nitrogen to stir the reaction overnight.Water (50 mL) was added to the reaction mixture, and the mixture was evaporated.The combined organic phases were washed with saturated brine (50 mL).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue obtained was purified by silica gel column chromatography.(pure petroleum ether) to give the title compound as a green solid(33 mg, 46%).
46% With bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere; 2,4,6-trichloropyrimidine (67 mg, 0.37 mmol) was dissolved in DMF (8 mL), thenbi s(triphenylphosphine)palladium(II) chloride (25 mg, 0.03 mmol) and<strong>[145214-05-7]2-(tributylstannyl)oxazole</strong> (120 mg, 0.34 mmol) were added into the mixture. The resulting mixture was stirred at 90 C under nitrogen protection overnight. To the reaction mixture was added water (50 mL), and the resulting mixture was extracted with ethyl acetate (50 mL x 3). The combined organic layers were washed with saturated brine (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (PE) to give the title compound as a green solid (33 mg, 46%).MS (ESI, pos.ion) m/z: 215.9 [M+H]t
27% With bis(triphenylphosphine)palladium(II) chloride; In N,N-dimethyl-formamide; at 90℃;Inert atmosphere; To a solution of 2.4.6-trichloropyrimidine (0.29 g, 1.60 mmol) in anhydrous DMF (10mL) were added bis(triphenylphosphine)palladium(II) chloride (99 mg, 0.14 mmol) and<strong>[145214-05-7]2-(tributylstannyl)oxazole</strong> (500 mg, 1.40 mmol). The mixture was stirred at 90 oc overnightunder nitrogen protection. To the reaction mixture was added water (30 mL), and the resultingmixture was extracted with ethyl acetate (30 mL x 3). The combined organic layers were washedwith saturated brine (50 mL x 3), dried over anhydrous sodium sulfate and filtered. The solventin the filtrate was removed and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 1011) to give the title compound as a white solid (80 mg, 27 %).1H NMR (400 MHz, CDCh) 8 (ppm): 8.07 (s, lH), 7.94 (s, lH), 7.46 (s, lH).
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