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CAS No. : | 648423-79-4 | MDL No. : | MFCD09054852 |
Formula : | C8H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WWUXGTVYEKCPJQ-UHFFFAOYSA-N |
M.W : | 164.16 | Pubchem ID : | 23082051 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
With diphenyl phosphoryl azide; triethylamine; In ethyl acetate; at 20.0℃; for 2.0h; | Into 10 ml of ethyl acetate was suspended 374 mg of <strong>[648423-79-4]2-cyclopropylpyrimidine-5-carboxylic acid</strong>, and then 345 mg of triethylamine and 690 mg of DPPA were added thereto, followed by 2 hours of stirring at room temperature. The reaction solution was washed with a saturated sodium bicarbonate aqueous solution and then water. After the solution was dried over anhydrous sodium sulfate, the solvent was removed by evaporation. Toluene was added thereto and the solvent was removed by evaporation to obtain 2-cyclopropylpyrimidine-5-carboxyl azide. The resulting acid azide was dissolved into 20 ml of toluene and the solution was heated and refluxed for 30 minutes to convert the acid azide into 2-cyclopropyl-5-isocyanatopyridine, followed by ice-cooling of the reaction solution. Into 3 ml of ethyl acetate was dissolved 500 mg of 4-[(2S,5R)-2,5-dimethylpiperazin-1-yl]-2-fluoro-6-methoxybenzonitrile, and the resulting solution was added dropwise to the above reaction solution, followed by 18 hours of stirring at room temperature. The reaction solution was evaporated and the resulting residue was subjected to silica gel column chromatography and a resulting oily product from an eluate using methanol-chloroform (3:97, v/v) was crystallized from ethyl acetate-diethyl ether to obtain 626 mg of the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With ammonium hydroxide; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20.0℃; | To a solution of <strong>[648423-79-4]2-cyclopropylpyrimidine-5-carboxylic acid</strong> (328 mg, CAS: 648423-79-4), HATU(836 mg, CAS: 148893-10-1) and Et3N (606 mg, CAS: 121-44-8) in DMF (2.0 mL) was added NH3 in water (25% ~28%, 1.0 mL) at room temperature. The reaction mixture was stirred overnight. Volatiles were removed under reduced pressure. The mixture was purified through reverse phase chromatography (C-18 column, mobile phase: A, H20; B, CH3CN with 0.5% NuEta3·Eta20) to give 2-cyclopropylpyrimidine-5-carboxamide as a white solid (241 mg, yield 74%). MS (ESI): 164.1 (M+H)+. |
74% | With ammonium hydroxide; triethylamine; HATU; In N,N-dimethyl-formamide; at 20.0℃; | a) 2-Cyclopropylpyrimidine-5-carboxamideTo a solution of <strong>[648423-79-4]2-cyclopropylpyrimidine-5-carboxylic acid</strong> (328 mg, CAS: 648423-79-4), HATU(836 mg, CAS: 148893-10-1) and Et3N (606 mg, CAS: 121-44-8) in DMF (2.0 mL) was added NH3 in water (25 % 28 %, 1.0 mL) at room temperature. The reaction was stuffed overnight. Volatiles were removed under reduced pressure. The mixture was purified through reverse phase chromatography (C-18 column, mobile phase: A, H20; B, CH3CN with 0.5 %NH3?H20) to give 2-cyclopropylpyrimidine-5-carboxamide as a white solid (241 mg, yield 74%). MS (ESI): 164.1 (M+H). |
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