2-cyclopropylethyl methanesulfonate

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution of 2-cyclopropylethanol (2.1 g, 24.4 mmol) in dichloromethane (50 ml) at 0° C. under nitrogen was added triethylamine (4.1 ml, 1.3 mol equiv). Methanesulphonyl chloride (2.5 ml, 1.3 mol equiv) was added dropwise and the reaction stirred for 16 hours at room temperature. Water (30 ml) and dichloromethane (30 ml) were added. The organic phase was washed with water (2×50 ml) and then dried over anhydrous MgSO4. The solution was then filtered and the solvent removed in vacuo to give the title compound as an oil (4.0 g). The organic phase was washed with water (2×50 ml) dried over anhydrous MgSO4 The solution was then filtered the solvent removed in vacuo

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

実験手順: A 0.5 g quantity of 2-cyclopropylethanol and 3.1 ml of triethylamine were dissolved in 10 ml of ethyl acetate, and 0.75 ml of methanesulfonyl chloride was added with ice-cooling and stirring. After stirring for 30 minutes, water was added to the reaction mixture and extraction was performed. The organic layer was washed with water twice and concentrated by removing the solvent under reduced pressure to give 1 g of pale yellow oily 2-cyclopropylethyl methanesulfonate. cooling After stirring for 30 minutes The organic layer was washed with water twice concentrated by removing the solvent under reduced pressure

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

実験手順: To a solution of 2-cyclopropylethanol (2.1 g, 24.4 mmol) in dichloromethane (50 ml) at 0° C. under nitrogen was added triethylamine (4.1 ml, 1.3 mol equiv). Methanesulphonyl chloride (2.5 ml, 1.3 mol equiv) was added dropwise and the reaction stirred for 16 hours at room temperature. Water (30 ml) and dichloromethane (30 ml) were added. The organic phase was washed with water (2×50 ml) and then dried over anhydrous MgSO4. The solution was then filtered and the solvent removed in vacuo to give the title compound as an oil (4.0 g). The organic phase was washed with water (2×50 ml) dried over anhydrous MgSO4 The solution was then filtered the solvent removed in vacuo

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

実験手順: To a solution of 2-cyclopropylethanol (2.1 g, 24.4 mmol) in dichloromethane (50 ml) at 0° C. under nitrogen was added triethylamine (4.1 ml, 1.3 mol equiv). Methanesulphonyl chloride (2.5 ml, 1.3 mol equiv) was added dropwise and the reaction stirred for 16 hours at room temperature. Water (30 ml) and dichloromethane (30 ml) were added. The organic phase was washed with water (2×50 ml) and then dried over anhydrous MgSO4. The solution was then filtered and the solvent removed in vacuo to give the title compound as an oil (4.0 g). The organic phase was washed with water (2×50 ml) dried over anhydrous MgSO4 The solution was then filtered the solvent removed in vacuo

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

実験手順: To a mixture of 2-cyclopropylethanol (5.35 g, 62.1 mmol) and dichloromethane (107 mL) were added methanesulfonyl chloride (5.29 mL, 68.3 mmol) and triethylamine (13.1 mL, 93.1 mmol) in that order while stirring on ice, and the resulting mixture was stirred for 1 hour. Water and ethyl acetate were then added to the reaction mixture. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (10.3 g, 62.7 mmol). the resulting mixture was stirred for 1 hour After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was then filtered the solvent in the filtrate was distilled off under reduced pressure

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

実験手順: To a mixture of 2-cyclopropylethanol (5.35 g, 62.1 mmol) and dichloromethane (107 mL) were added methanesulfonyl chloride (5.29 mL, 68.3 mmol) and triethylamine (13.1 mL, 93.1 mmol) in that order while stirring on ice, and the resulting mixture was stirred for 1 hour. Water and ethyl acetate were then added to the reaction mixture. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent in the filtrate was distilled off under reduced pressure to obtain the title compound (10.3 g, 62.7 mmol). the resulting mixture was stirred for 1 hour After thoroughly shaking the mixture the organic layer was separated the organic layer was washed with brine dried over anhydrous magnesium sulfate The mixture was then filtered the solvent in the filtrate was distilled off under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (19.81 g, 131.98 mmol) in acetonitrile (520 ml) were added intermediate 1 (34.36 g, 171.57 mmol) and potassium carbonate (56.73 g, 410.3 mmol) and the mixture was heated at 105° C. for 12 hours. The mixture was cooled to room temperature and the solid was filtered off The filtrate was evaporated till dryness. The crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 3 (13.18 g, 46%). The mixture was cooled to room temperature the solid was filtered off The filtrate was evaporated till dryness The crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent) The desired fractions were collected evaporated in vacuo

反応条件: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-methoxy-2-oxo-1,2-dihydro-pyridine-3-carbonitrile (19.81 g, 131.98 mmol) in acetonitrile (520 ml) were added intermediate 1 (34.36 g, 171.57 mmol) and potassium carbonate (56.73 g, 410.3 mmol) and the mixture was heated at 105° C. for 12 hours. The mixture was cooled to room temperature and the solid was filtered off The filtrate was evaporated till dryness. The crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 3 (13.18 g, 46%). The mixture was cooled to room temperature the solid was filtered off The filtrate was evaporated till dryness The crude product was purified by column chromatography (silica gel; DCM to DCM/EtOAc up to 20% as eluent) The desired fractions were collected evaporated in vacuo

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

実験手順: 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.5 g, 6.64 mmol), sodium carbonate (844 mg, 7.9 mmol) and 2-cyclopropylethyl methanesulfonate (1.19 g, 7.3 mmol) were stirred in dimethylformamide (25 ml, dry) for two days at 80° C. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed with hydrochloric acid (2N), brine, dried (MgSO4) and then evaporated to dryness. The crude product was triturated with ether and the solid collected by filtration to afford the title compound as a white solid (0.96 g, 49%). m/z 295 [MH+]. The reaction mixture was partitioned between ethyl acetate and water The organic phase was separated washed with hydrochloric acid (2N), brine dried (MgSO4) evaporated to dryness The crude product was triturated with ether the solid collected by filtration

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

実験手順: 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.5 g, 6.64 mmol), sodium carbonate (844 mg, 7.9 mmol) and 2-cyclopropylethyl methanesulfonate (1.19 g, 7.3 mmol) were stirred in dimethylformamide (25 ml, dry) for two days at 80° C. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed with hydrochloric acid (2N), brine, dried (MgSO4) and then evaporated to dryness. The crude product was triturated with ether and the solid collected by filtration to afford the title compound as a white solid (0.96 g, 49%). m/z 295 [MH+]. The reaction mixture was partitioned between ethyl acetate and water The organic phase was separated washed with hydrochloric acid (2N), brine dried (MgSO4) evaporated to dryness The crude product was triturated with ether the solid collected by filtration