4-methoxy-3-(2-morpholin-4-ylethoxy)benzaldehyde

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.25 g, 5.63 mmol), 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde (1.64 g), and xylenes (12 ml) was heated at 160° C. overnight. Additional aldehyde (0.5 g) was added and the mixture was refluxed until complete, then cooled to room temperature. The solvent was stripped, the residue was slurried with EtOAc and the product was collected by filtration and combined with the product from a similar experimental run. The combined product was recrystallized from CH3CN to afford 1-cyclopentyl-3-ethyl-6-[4-methoxy-3-[2-(4-morpholinyl)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 205-206° C. the mixture was refluxed until complete, then cooled to room temperature the product was collected by filtration The combined product was recrystallized from CH3CN

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-hydroxy-4-methoxybenzaldehyde (8.56 g, 56.26 mmol) in CH3CN (50 ml) was added K2CO3 (17.1 g) with CH3CN (20 ml), followed 20 minutes later by N-(2-chloroethyl)morpholine hydrochloride (11.52 g). The reaction mixture was refluxed overnight, and then was cooled to room temperature, filtered, and the solvent was stripped to give, as an amber oil, 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde. The reaction mixture was refluxed overnight filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-hydroxy-4-methoxybenzaldehyde (8.56 g, 56.26 mmol) in CH3CN (50 ml) was added K2CO3 (17.1 g) with CH3CN (20 ml), followed 20 minutes later by N-(2-chloroethyl)morpholine hydrochloride (11.52 g). The reaction mixture was refluxed overnight, and then was cooled to room temperature, filtered, and the solvent was stripped to give, as an amber oil, 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde. The reaction mixture was refluxed overnight filtered

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.25 g, 5.63 mmol), 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde (1.64 g), and xylenes (12 ml) was heated at 160° C. overnight. Additional aldehyde (0.5 g) was added and the mixture was refluxed until complete, then cooled to room temperature. The solvent was stripped, the residue was slurried with EtOAc and the product was collected by filtration and combined with the product from a similar experimental run. The combined product was recrystallized from CH3CN to afford 1-cyclopentyl-3-ethyl-6-[4-methoxy-3-[2-(4-morpholinyl)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 205°-206° C. the mixture was refluxed until complete, then cooled to room temperature the product was collected by filtration The combined product was recrystallized from CH3CN

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-hydroxy-4-methoxybenzaldehyde (8.56 g, 56.26 mmol) in CH3CN (50 ml) was added K2CO3 (17.1 g) with CH3CN (20 ml), followed 20 minutes later by N-(2-chloroethyl)morpholine hydrochloride (11.52 g). The reaction mixture was refluxed overnight, and then was cooled to room temperature, filtered, and the solvent was stripped to give, as an amber oil, 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde. The reaction mixture was refluxed overnight filtered

反応条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.25 g, 5.63 mmol), 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde (1.64 g), and xylenes (12 ml) was heated at 160° C. overnight. Additional aldehyde (0.5 g) was added and the mixture was refluxed until complete, then cooled to room temperature. The solvent was stripped, the residue was slurried with EtOAc and the product was collected by filtration and combined with the product from a similar experimental run. The combined product was recrystallized from CH3CN to afford 1-cyclopentyl-3-ethyl-6-[4-methoxy-3-[2-(4-morpholinyl)ethoxy]phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 205-206° C. the mixture was refluxed until complete, then cooled to room temperature the product was collected by filtration The combined product was recrystallized from CH3CN

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 3-hydroxy-4-methoxybenzaldehyde (8.56 g, 56.26 mmol) in CH3CN (50 ml) was added K2CO3 (17.1 g) with CH3CN (20 ml), followed 20 minutes later by N-(2-chloroethyl)morpholine hydrochloride (11.52 g). The reaction mixture was refluxed overnight, and then was cooled to room temperature, filtered, and the solvent was stripped to give, as an amber oil, 4-methoxy-3-[2-(4-morpholinyl)ethoxy]benzaldehyde. The reaction mixture was refluxed overnight filtered