3-氨基丁腈

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

实验步骤: A mixture of 14.5 g (0.1 moles) of 3-chloro-6-pyridazinyl-hydrazine, 8.5 g (0.1 moles) of 3-iminobutyronitrile and 150 ml of ethanol is heated to reflux for 9 hours. After cooling the separated crystals are filtered, washed with ethanol and dried. Yield: 15.6 g (74.0%); m.p.: 148°-150° C. The hydrochloride melts at 157°-159° C. is heated to reflux for 9 hours After cooling the separated crystals are filtered washed with ethanol dried

反应条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of (6-Methylsulfanyl-pyrimidin-4-yl)-hydrazine (1.0 g, 6.4 mmol), 3-Imino-butyronitrile (1.1 g, 12.8 mmol), and ethanol (30 mL) is heated to 85° C. for overnight. The reaction mixture is then cooled to room temperature, condensed, and treated with 75 mL ethyl acetate. The reaction mixture is partitioned between ethyl acetate and aqueous layer. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80% to afford 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine: 1H NMR 400 MHz (d6-DMSO) δ 8.72 (s, 1H), 7.53 (s, 1H), 6.90 (s, 1H), 5.26 (s, 1H), 2.57 (s, 3H), 2.08 (s, 3H); MS m/z 222.07 (M+1). The reaction mixture is then cooled to room temperature condensed The reaction mixture is partitioned between ethyl acetate and aqueous layer The organic layer is dried over Na2SO4 concentrated The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80%

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

实验步骤: A mixture of 14.5 g (0.1 moles) of 3-chloro-6-pyridazinyl-hydrazine, 8.5 g (0.1 moles) of 3-iminobutyronitrile and 150 ml of ethanol is heated to reflux for 9 hours. After cooling the separated crystals are filtered, washed with ethanol and dried. Yield: 15.6 g (74.0%); m.p.: 148°-150° C. The hydrochloride melts at 157°-159° C. is heated to reflux for 9 hours After cooling the separated crystals are filtered washed with ethanol dried

反应条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of (6-Methylsulfanyl-pyrimidin-4-yl)-hydrazine (1.0 g, 6.4 mmol), 3-Imino-butyronitrile (1.1 g, 12.8 mmol), and ethanol (30 mL) is heated to 85° C. for overnight. The reaction mixture is then cooled to room temperature, condensed, and treated with 75 mL ethyl acetate. The reaction mixture is partitioned between ethyl acetate and aqueous layer. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80% to afford 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine: 1H NMR 400 MHz (d6-DMSO) δ 8.72 (s, 1H), 7.53 (s, 1H), 6.90 (s, 1H), 5.26 (s, 1H), 2.57 (s, 3H), 2.08 (s, 3H); MS m/z 222.07 (M+1). The reaction mixture is then cooled to room temperature condensed The reaction mixture is partitioned between ethyl acetate and aqueous layer The organic layer is dried over Na2SO4 concentrated The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80%

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

实验步骤: A mixture of 14.5 g (0.1 moles) of 3-chloro-6-pyridazinyl-hydrazine, 8.5 g (0.1 moles) of 3-iminobutyronitrile and 150 ml of ethanol is heated to reflux for 9 hours. After cooling the separated crystals are filtered, washed with ethanol and dried. Yield: 15.6 g (74.0%); m.p.: 148°-150° C. The hydrochloride melts at 157°-159° C. is heated to reflux for 9 hours After cooling the separated crystals are filtered washed with ethanol dried

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

实验步骤: By substituting 1-phenylethyl-4-hydrazino-1H-pyrazolo-[3,4-b]-pyridine-5-carboxylic acid, methyl ester for the 1-ethyl-4-hydrazino-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid, ethyl ester and 2-iminomethylpentanonitrile for the 3-iminobutyronitrile in the procedure of Example 1 a and proceeding as in parts b and c, 3-propyl-8-phenylethyl-4H-pyrazolo[1,5-a]pyrazolo4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one and 4-methyl-8-phenylethyl-3-propyl-4H-pyrazolo-[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one, respectively, are obtained.

反应条件: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The mixture of (6-Methylsulfanyl-pyrimidin-4-yl)-hydrazine (1.0 g, 6.4 mmol), 3-Imino-butyronitrile (1.1 g, 12.8 mmol), and ethanol (30 mL) is heated to 85° C. for overnight. The reaction mixture is then cooled to room temperature, condensed, and treated with 75 mL ethyl acetate. The reaction mixture is partitioned between ethyl acetate and aqueous layer. The organic layer is dried over Na2SO4 and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80% to afford 5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine: 1H NMR 400 MHz (d6-DMSO) δ 8.72 (s, 1H), 7.53 (s, 1H), 6.90 (s, 1H), 5.26 (s, 1H), 2.57 (s, 3H), 2.08 (s, 3H); MS m/z 222.07 (M+1). The reaction mixture is then cooled to room temperature condensed The reaction mixture is partitioned between ethyl acetate and aqueous layer The organic layer is dried over Na2SO4 concentrated The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 10% to 80%