3-乙基-2,4-戊二酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared according to the procedure described in step 1 of Example 1 from 3-ethyl-2,4-pentanedione and 2-(4-hydrazinophenyl)ethanol hydrochloride: MS (ESI) m/z 245 [M+H]+, 1H-NMR (CDCl3) δ 7.36-7.26 (4H, m), 3.84 (2H, t, J=6.6 Hz), 2.89 (2H, t, J=6.6 Hz), 2.24 (2H, q, J=7.5 Hz), 2.26 (3H, s), 2.22 (3H, s), 1.12 (3H, t, J=7.5 Hz).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared according to the procedure described in step 1 of Example 1 from 3-ethyl-2,4-pentanedione and 2-(4-hydrazinophenyl)ethanol hydrochloride: MS (ESI) m/z 245 [M+H]+, 1H-NMR (CDCl3) δ 7.36-7.26 (4H, m), 3.84 (2H, t, J=6.6 Hz), 2.89 (2H, t, J=6.6 Hz), 2.24 (2H, q, J=7.5 Hz), 2.26 (3H, s), 2.22 (3H, s), 1.12 (3H, t, J=7.5 Hz).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: At room temperature, to a mixture of 3-ethyl-2,4-pentanedione 5 g and ethanol 50 ml was added hydrazine one hydrate 2.9 g and the resulting mixture was stirred for five hours. The ethanol was distilled off and the resulting residue was subjected to a silica gel column chromatography to give 3,5-dimethyl-4-ethyl-1H-pyrazole 6.0 g. The ethanol was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In N2 atmosphere free of water and oxygen, to a reactor were successively added 0.024 mol LiAlH4 and 100 ml THF, followed by adding dropwise 0.04 mol 3-ethyl-2,4-pentandione while cooling the mixture with ice-bath. The reaction was allowed to continue at room temperature for 48 hours. Aqueous solution of sodium hydroxide was added carefully to stop the reaction. The reaction mixture was filtered and the cake was washed with anhydrous ethyl ether for three times. The organic phase was combined and dried over anhydrous sodium sulfate. Removing the solvent gave 3.4 g product. while cooling the mixture with ice-bath the reaction The reaction mixture was filtered the cake was washed with anhydrous ethyl ether for three times dried over anhydrous sodium sulfate Removing the solvent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a three-neck flask in N2 atmosphere free of water and oxygen were successively added 0.066 mol potassium tert-butoxide and 150 mlTHF. Then to the resulting mixture was slowly added dropwise 0.06 mol acetylacetone with stirring while cooling the mixture with ice-bath. The reaction was allowed to continue at room temperature for 1 hour, then 0.07 mol iodoethane was added dropwise at room temperature. Next, the reaction was allowed to continue at room temperature for further 48 hours. After the reaction was finished, the solvent was removed by distillation. To the solid mixture was added saturated saline until the solid mixture was just completely dissolved. The solution was extracted with suitable amount of anhydrous ethyl ether for three times. The organic phase was combined and dried over anhydrous sodium sulfate. The solvent was removed to give 6.5 g product. while cooling the mixture with ice-bath to continue at room temperature for further 48 hours the solvent was removed by distillation To the solid mixture was added saturated saline until the solid mixture was just completely dissolved The solution was extracted with suitable amount of anhydrous ethyl ether for three times dried over anhydrous sodium sulfate The solvent was removed

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In N2 atmosphere free of water and oxygen, to a reactor were successively added 0.024 mol LiAlH4 and 100 ml THF, followed by adding dropwise 0.04 mol 3-ethyl-2,4-pentandione while cooling the mixture with ice-bath. The reaction was allowed to continue at room temperature for 48 hours. Aqueous solution of sodium hydroxide was added carefully to stop the reaction. The reaction mixture was filtered and the cake was washed with anhydrous ethyl ether for three times. The organic phase was combined and dried over anhydrous sodium sulfate. Removing the solvent gave 3.4 g product. while cooling the mixture with ice-bath the reaction The reaction mixture was filtered the cake was washed with anhydrous ethyl ether for three times dried over anhydrous sodium sulfate Removing the solvent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a three-neck flask in N2 atmosphere free of water and oxygen were successively added 0.066 mol potassium tert-butoxide and 150 mlTHF. Then to the resulting mixture was slowly added dropwise 0.06 mol acetylacetone with stirring while cooling the mixture with ice-bath. The reaction was allowed to continue at room temperature for 1 hour, then 0.07 mol iodoethane was added dropwise at room temperature. Next, the reaction was allowed to continue at room temperature for further 48 hours. After the reaction was finished, the solvent was removed by distillation. To the solid mixture was added saturated saline until the solid mixture was just completely dissolved. The solution was extracted with suitable amount of anhydrous ethyl ether for three times. The organic phase was combined and dried over anhydrous sodium sulfate. The solvent was removed to give 6.5 g product. while cooling the mixture with ice-bath to continue at room temperature for further 48 hours the solvent was removed by distillation To the solid mixture was added saturated saline until the solid mixture was just completely dissolved The solution was extracted with suitable amount of anhydrous ethyl ether for three times dried over anhydrous sodium sulfate The solvent was removed

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To aminoguanidine hydrochloride (1.76 g, 15.9 mmol), water (5 ml), sodium hydroxide (636 mg, 15.9 mmol), and 3-ethyl-2,4-pentanedione (manufactured by Tokyo Chemical Industry, purity: 90.0% or higher) (4.50 g, 35.0 mmol) were added, and then stirred at 80° C. for 8 hours. To the reaction mixture, water (30 ml) was added, and then stirred at 0° C. for 1 hour. The precipitated crystals were collected by filtration, washed with water, and dried under reduced pressure to obtain 5-ethyl-2-(4-ethyl-3,5-dimethylpyrazol-1-yl)-4,6-dimethylpyrimidine (1.35 g, 33%). stirred at 0° C. for 1 hour The precipitated crystals were collected by filtration washed with water dried under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3-amino-2,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester (0.6 g; 2.68 mmol; 1 eq.) and 3-ethyl-2,4-pentanedione (0.36 mL; 2.68 mmol; 1 eq.) in AcOH (8 mL) was stirred at room temperature for 32 hours. Aq. 32% HCl (1.05 mL; 10.7 mmol; 4 eq.) was added and the resulting mixture stirred for a further 16 hours. After concentration in vacuo, the residue was triturated in MTBE and the precipitate filtered off and dried. The solid was taken up in ethyl acetate and washed with 1M aq. NaOH (2×), dried over magnesium sulfate and concentrated in vacuo to afford the title compound (450 mg, 94%) as a beige solid. 1H NMR (DMSO-d6) δ 4.05-4.00 (m, 4H), 2.73-2.63 (m, 5H), 2.51 (s, 3H), 1.12 (t, J=7.4 Hz, 3H). UPLC/MS: (MS+) 217.3 ([M+H]+). the resulting mixture stirred for a further 16 hours After concentration in vacuo the residue was triturated in MTBE the precipitate filtered off dried washed with 1M aq. NaOH (2×) dried over magnesium sulfate concentrated in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared according to the procedure described in step 1 of Example 1 from 3-ethyl-2,4-pentanedione and 2-(4-hydrazinophenyl)ethanol hydrochloride: MS (ESI) m/z 245 [M+H]+, 1H-NMR (CDCl3) δ 7.36-7.26 (4H, m), 3.84 (2H, t, J=6.6 Hz), 2.89 (2H, t, J=6.6 Hz), 2.24 (2H, q, J=7.5 Hz), 2.26 (3H, s), 2.22 (3H, s), 1.12 (3H, t, J=7.5 Hz).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: At room temperature, to a mixture of 3-ethyl-2,4-pentanedione 5 g and ethanol 50 ml was added hydrazine one hydrate 2.9 g and the resulting mixture was stirred for five hours. The ethanol was distilled off and the resulting residue was subjected to a silica gel column chromatography to give 3,5-dimethyl-4-ethyl-1H-pyrazole 6.0 g. The ethanol was distilled off

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In N2 atmosphere free of water and oxygen, to a reactor were successively added 0.024 mol LiAlH4 and 100 ml THF, followed by adding dropwise 0.04 mol 3-ethyl-2,4-pentandione while cooling the mixture with ice-bath. The reaction was allowed to continue at room temperature for 48 hours. Aqueous solution of sodium hydroxide was added carefully to stop the reaction. The reaction mixture was filtered and the cake was washed with anhydrous ethyl ether for three times. The organic phase was combined and dried over anhydrous sodium sulfate. Removing the solvent gave 3.4 g product. while cooling the mixture with ice-bath the reaction The reaction mixture was filtered the cake was washed with anhydrous ethyl ether for three times dried over anhydrous sodium sulfate Removing the solvent