Alternatived Products of [ 883230-68-0 ]
Product Details of [ 883230-68-0 ]
| CAS No. : | 883230-68-0 |
MDL No. : | MFCD08064043 |
| Formula : |
C7H5BrN4
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | SCDMEQDXMQROEY-UHFFFAOYSA-N |
| M.W : | 225.05 |
Pubchem ID : | 16414245 |
| Synonyms : |
|
Safety of [ 883230-68-0 ]
Application In Synthesis of [ 883230-68-0 ]
* 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.
- Upstream synthesis route of [ 883230-68-0 ]
- Downstream synthetic route of [ 883230-68-0 ]
- 1
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[ 288-32-4 ]
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[ 32779-36-5 ]
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[ 883230-68-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
With potassium carbonate In dimethyl sulfoxide at 70℃; for 24h; Inert atmosphere; |
|
|
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; |
To a solution of 5-bromo-2-chloropyrimidine (1.02 g) in N-methylpyrrolidine-2- one (10 mL) was added lH-imidazole (680 mg) and potassium carbonate (2.74 g) and refluxed overnight at 80 0C. The reaction mixture was poured in water and extracted with dichloromethane, washed with brine and dried over anhydrous sodium sulfate. Solvent was removed under vacuum and to the product thus obtained was added cold ethanol which afforded the title compound (200 mg).EIMS (m/z): 225 (M+H) |
|
Stage #1: 1H-imidazole With sodium hydride In dimethyl sulfoxide at 20℃; for 0.166667h;
Stage #2: 5-Bromo-2-chloropyrimidine In dimethyl sulfoxide for 1h; |
D1
D1. 5-Bromo-2-imidazol-1-yl-pyrimidine; 280 mg of sodium hydride (strength 60 Vol%) are suspended in 5.0 ml of DMSO under an atmosphere of dry nitrogen. Subsequently, a solution of 409 mg of imidazole in 5.0 ml of DMSO is added dropwise at room temperature. After the gas evolution has ceased, the reaction mixture is stirred for further 10 min. Thereafter, a solution of 987 mg of 5-bromo-2-chloro-pyrimidine in 10 ml of DMSO is added dropwise to the reaction mixture. The yellow suspension is stirred for 1 hour. For workup, the reaction mixture is poured into 150 ml of iced water and the suspension is filtered with suction. The residue is rinsed with water and dried to yield 1.11 g of the title compound as a colorless solid. M. p. 2260C. ESI- MS: 225.2/227.2 (MH+). TLC: Rf = 0.50 (dichloromethane/methanol 20:1 parts per volume). |
Reference：
[1]Wang, Lei; Liu, Ning; Dai, Bin
[RSC Advances, 2015, vol. 5, # 100, p. 82097 - 82111]
[2]Current Patent Assignee: SUN PHARMACEUTICAL INDUSTRIES LIMITED - WO2006/38100, 2006, A1
Location in patent: Page/Page column 70
[3]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2007/39581, 2007, A1
Location in patent: Page/Page column 31-32
- 2
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[ 854373-97-0 ]
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[ 883230-68-0 ]
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[ 1043906-22-4 ]
- 3
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[ 288-32-4 ]
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[ 183438-24-6 ]
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[ 883230-68-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 65% |
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere; |
|
- 4
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[ 883230-68-0 ]
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[ 1122-91-4 ]
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[ 933043-73-3 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 5-bromo-2-(1H-imidazol-1-yl)pyrimidine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: 4-bromo-benzaldehyde In tetrahydrofuran for 48h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water |
C1
C1. 1-(4-Bromo-phenyl)-1-(2-imidazol-1-yl-pyrimidin-5-yl)-methanol; 22.5 g of 5-bromo-2-imidazol-1-yl-pyrimidine (compound D1 ) are dissolved in 250 ml of tetrahydrofuran under an atmosphere of dry nitrogen. Subsequently, the reaction mixture is cooled in an ice bath and 70 ml of isopropylmagnesium chloride (strength 2.0 M in tetrahydrofurane) are added dropwise. Thereafter, the solution is allowed to warm up to room temperature and stirred for 30 min.Subsequently, a solution of 14.8 g of 4-bromo-benzaldehyde in 50 ml of tetrahydrofurane is added dropwise and stirring is continued for 48 hours. For workup, the reaction mixture is poured into 300 ml of water. The solution is subsequently acidified to pH 5 using hydrochloric acid (strength 1.0 N), extracted three times with each 100 ml of dichloromethane, dried using Na2SO4, filtered with suction, and evaporated to dryness. The remaining crude material is purified by flash chromatography (eluent gradient: dichloromethane/ethanol 0.0-5.0 Vol%) to afford 11.19 g of the title compound as a colorless solid. M. p. 2270C. ESI-MS: 331.3/333.2 (MH+). TLC: Rf = 0.29 (dichloromethane/ethanol 20:1 ). |
- 5
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[ 883230-68-0 ]
-
2-methylcyclopentyl trifluoroborate
[ No CAS ]
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trans-2-(1H-imidazol-1-yl)-5-(2-methylcyclopentyl)pyrimidine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 69% |
With (1,2-dimethoxyethane)dichloronickel(II); Ir(dF(CF3)ppy)2(bpy)PF6; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran; 1,4-dioxane at 24℃; for 24h; Inert atmosphere; Sealed tube; Irradiation; |
|
- 6
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[ 883230-68-0 ]
-
potassium α-benzyloxymethyltrifluoroborate
[ No CAS ]
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5-((benzyloxy)methyl)-2-(1H-imidazol-1-yl)pyrimidine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 83% |
With dipotassium hydrogenphosphate; (1,2-dimethoxyethane)dichloronickel(II); Ir[dFCF3ppy]2(bpy)*PF6; 4,4'-di-tert-butyl-2,2'-bipyridine In 1,4-dioxane; N,N-dimethyl acetamide at 24℃; for 24h; Irradiation; Inert atmosphere; |
|
- 7
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[ 288-13-1 ]
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[ 883230-68-0 ]
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[ 883230-94-2 ]
| Yield | Reaction Conditions | Operation in experiment |
| 53% |
With caesium carbonate; copper(II) nitrate In N,N-dimethyl-formamide at 130℃; for 24h; Schlenk technique; chemoselective reaction; |
Copper-Catalyzed C-N Bond Exchange; General Procedure
General procedure: The 2-substituted 5-halopyridine or 5-halopyrimidine substrate (0.5 mmol), an N-heterocyclic amine (1.0 mmol), Cu(NO3)2 (0.1 mmol) and Cs2CO3 (1.0 mmol) were added to a 25-mL Schlenk tube, followed by addition of DMF (2 mL). This mixture was stirred at 130 °C or 140 °C (see schemes and tables) under air atmosphere for 24 h. Then, the reaction mixture was added to brine (15 mL) and this mixture was extracted with CH2Cl2 (3 × 15 mL). The combined extracts were concentrated under reduced pressure and the product was isolated by flash chromatography on a silica gel (200-300 mesh) column. |
Reference：
[1]Tao, Sheng; Ji, Enhui; Shi, Lei; Liu, Ning; Xu, Liang; Dai, Bin
[Synthesis, 2017, vol. 49, # 23, p. 5120 - 5130]
- 8
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[ 288-32-4 ]
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[ 62802-38-4 ]
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[ 883230-68-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 95% |
With potassium carbonate; In dimethyl sulfoxide; at 70℃; for 24h;Schlenk technique; |
General procedure: 5-Bromo-2-fluoropyridine (0.5 mmol), an N-heterocyclic amine (1.0 mmol) and K2CO3 (1.0 mmol) were added to a 25-mL Schlenk tube, followed by addition of DMSO (2 mL). The reaction mixture was heated to 70 C for 24 h under air atmosphere. Then, the reaction mixture was added to brine (15 mL) and this mixture was extracted with CH2Cl2 (3 × 15 mL). The combined extracts were concentrated under reduced pressure and the product was isolated by flash chromatography on a silica gel (200-300 mesh) column. |
- 9
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[ 269409-73-6 ]
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[ 883230-68-0 ]
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3-(2-(1H-imidazol-1-yl)pyrimidin-5-yl)benzoic acid
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 72% |
With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere; |
General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 mol%) and further degassed (5times). The resulting mixture was stirred at 95 C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100%) to yield the desired product. |
- 10
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[ 883230-68-0 ]
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potassium trifluoro(3,3,3-trifluoroprop-1-en-2-yl)borate
[ No CAS ]
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2-(1H-imidazol-1-yl)-5-(3,3,3-trifluoroprop-1-en-2-yl)pyrimidine
[ No CAS ]
| Yield | Reaction Conditions | Operation in experiment |
| 53% |
With (2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-N-methylamino-1,1′-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In tetrahydrofuran; water at 80℃; for 18h; |
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