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CAS No. : | 7560-83-0 | MDL No. : | MFCD00014289 |
Formula : | C13H25N | Boiling Point : | - |
Linear Structure Formula : | CH3N(C6H11)2 | InChI Key : | GSCCALZHGUWNJW-UHFFFAOYSA-N |
M.W : | 195.34 | Pubchem ID : | 24210 |
Synonyms : |
|
Chemical Name : | N-Cyclohexyl-N-methylcyclohexanamine |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P501-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 | UN#: | 2735 |
Hazard Statements: | H302-H314 | Packing Group: | Ⅲ |
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 |
---|---|---|
178 mg (56%) | tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; | Step A (2E)-3-(2-Phenyl-5-pyrimidinyl)-2-propenoic Acid Methyl Ester Dioxane (1.3 mL) was added to a mixture of <strong>[38696-20-7]5-bromo-2-phenylpyrimidine</strong> (310 mg, 1.32 mmol, prepared as described in Org. Lett. 2002, 4, 513), tri-t-butylphosphonium tetrafluoroborate (11 mg, 0.038 mmol), and tris(dibenzylideneacetone)dipalladium(0) (18 mg, 0.020 mmol). N-Methyldicyclohexylamine (0.31 mL, 1.45 mmol) and methyl acrylate (0.24 mL, 2.67 mmol) were added and the mixture was stirred for 72 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. The residue was triturated with 5:1 hexane/ethyl acetate and the solid was filtered and dried in vacuo to provide 178 mg (56percent) of the title compound as an off-white solid. MS 241 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.47 g (70%) | tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; | Step A (2E)-3-[4-(2-Pyrimidinyl)phenyl]-2-butenoic Acid Ethyl Ester Dioxane (2 mL) was added to a mixture of 2-(4-bromophenyl)pyrimidine (0.59 g, 2.51 mmol, prepared as described in U.S. Pat. No. 5,780,473), tri-t-butylphosphonium tetrafluoroborate (36 mg, 0.12 mmol), and tris(dibenzylideneacetone)dipalladium(0) (57 mg, 0.062 mmol). N-Methyldicyclohexylamine (0.64 mL, 2.99 mmol) and ethyl crotonate (0.62 mL, 4.99 mmol) were added and the mixture was stirred for 18 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. Purification by chromatography (SiO2, 5:1 hexane/ethyl acetate) provided 0.47 g (70percent) of the title compound as an off-white solid. MS 269 (M+H)+. |
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