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CAS No. : | 101079-62-3 | MDL No. : | MFCD00955650 |
Formula : | C5H5ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IRYLYRQCDCQZHE-UHFFFAOYSA-N |
M.W : | 144.56 | Pubchem ID : | 4366471 |
Synonyms : |
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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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5.1 g | With potassium carbonate; In acetone; at 20℃; | Step 1: 6-Chloro-3-methylpyrimidin-4(3H)-one A mixture of <strong>[4765-77-9]6-chloropyrimidin-4(3H)-one</strong> (5 g), methyliodide (2.6 mL) and K2CO3 (10.6 g) in acetone (100 mL) is stirred at room temperature over night. The mixture is partitioned between water and ethyl acetate. The organic phase is washed with brine, dried (MgSO4) and concentrated. The residue is triturated with diisopropylether to give the title compound. Yield: 5.1 g; LC (method 11): tR=0.25 min; Mass spectrum (ESI+): m/z=145 [M+H]+. |
5.1 g | With potassium carbonate; In acetone; at 20℃; | A mixture of <strong>[4765-77-9]6-chloropyrimidin-4(3H)-one</strong> (5 g), methyliodide (2.6 mL) and K2CO3 (10.6 g) in acetone (100 mL) is stirred at room temperature over night. The mixture is partitioned between water and ethyl acetate. The organic phase is washed with brine, dried (MgSO4) and concentrated. The residue is triturated with diisopropylether to give the title compound. Yield: 5.1 g; LC (method 1 1 ): tR = 0.25 min; Mass spectrum (ESI+): m/z = 145 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.6 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 65℃; for 12h;Inert atmosphere; Sealed tube; | Step 2: 6-(4-Amino-3,5-dimethylphenyl)-3-methylpyrimidin-4(3H)-one In a microwave vial 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (5.6 g) and <strong>[101079-62-3]6-chloro-3-methylpyrimidin-4(3H)-one</strong> (3 g) are suspended in N,N-dimethylformamide (30 mL) and Na2CO3 (26 mL of a 2M aqueous solution). The mixture is purged for 5 minutes with argon. [1,1'-Bis(diphenylphosphino)-ferrocene]-dichloropalladium dichloromethane complex (508 mg) is added, the vial is sealed and the mixture is stirred at 65 C. for 12 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated to give the title compound. Yield: 2.6 g; LC (method 11): tR=0.71 min; Mass spectrum (ESI+): m/z=230 [M+H]+. |
2.6 g | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 65℃; for 12h;Inert atmosphere; Sealed tube; Microwave irradiation; | In a microwave vial 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)aniline (5.6 g) and <strong>[101079-62-3]6-chloro-3-methylpyrimidin-4(3H)-one</strong> (3 g) are suspended in N,N-dimethylformamide (30 mL) and Na2CO3 (26 mL of a 2M aqueous solution). The mixture is purged for 5 minutes with argon. [1 ,1 '-Bis(diphenylphosphino)-ferrocene]- dichloropalladium dichloromethane complex (508 mg) is added, the vial is sealed and the mixture is stirred at 65C for 12 hours. After cooling to room temperature the mixture is Partitioned between water and ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with brine and dried (MgSO4). The solvents are evaporated to give the title compound. Yield: 2.6 g; LC (method 1 1 ): tR = 0.71 min; Mass spectrum (ESI+): m/z = 230 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | 1. To a suspension of NaH (387 mg, 9.68 mmol, 60% oil dispersion) in dry DMSO (20 mL) at rt was added t-butyl cyanoacetate (1.37 g, 9.68 mmol), after stirring for 2 h, 6-chloro-3- methylpyrimidin-4(3H)-one (700 mg, 4.84 mmol) was added to the resulting mixture, the mixture was stirred at 120 C for 3 h. After cooling, the mixture was poured into saturated ammonium chloride solution, the resulting precipitates were collected by filtration, washed with water to give the title compounds as brown solid (650 mg, 54%); 2. To a solution of tert-butyl 2-cyano-2-(l-methyl-6-oxo-l,6- dihydropyrimidin-4-yl)acetate (650 mg, 2.61 mmol) in toluene (20 mL) was added TsOH (225 mg, 1.30 mmol). The resulting solution was stirred under reflux 6 h. After cooling, the solvent was removed. The residue was purified via silica chromatography and a gradient of 0 -10 % MeOH in DCM to afford the title compound as a yellow solid (200 mg, 51 %). |
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