Alternatived Products of [ 149806-11-1 ]
Product Details of [ 149806-11-1 ]
CAS No. : | 149806-11-1 |
MDL No. : | MFCD06589847 |
Formula : |
C10H13N3O
|
Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
191.23
|
Pubchem ID : | - |
Synonyms : |
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Safety of [ 149806-11-1 ]
Application In Synthesis of [ 149806-11-1 ]
* 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.
- Downstream synthetic route of [ 149806-11-1 ]
- 1
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[ 33513-42-7 ]
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[ 57356-64-6 ]
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[ 149806-11-1 ]
Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - -70℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h; |
8.II
To a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid. |
|
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - 70℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h;
Stage #3: With ammonium chloride In tetrahydrofuran; hexanes; water |
17; 8.II
To a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid. |
|
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - -70℃; for 1h;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h; |
8.II; 4
To a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid. |
|
Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexanes at -78 - -70℃;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -70℃; for 1h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes |
8.II
Part II: Preparation of 2-piperidin-1-yl-pyrimidine-5-carbaldehydeTo a solution of 5-bromo-2-piperidin-1-yl-pyrimidine (1.3 g, 5.4 mmol) in anhydrous tetrahydrofuran (30 mL) at -78°C was added 1.6 M n-butyl lithium in hexanes (3.7 mL, 5.93 mmol). The mixture was stirred at a temperature below -70°C for 1 hour. Dimethylformamide (4.2 mL, 53.9 mmol) was added dropwise and the reaction was stirred at a temperature below -70°C for 1 hour. The reaction was quenched with saturated ammonium chloride (10 mL), diluted with water (20 mL) and extracted with ethyl acetate (2 x 20 ml_). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the solvent removed under reduced pressure to provide a viscous brown oil. Flash chromatography (silica gel; 5-30% ethyl acetate in hexanes) provided 2-piperidin-1-yl-pyrimidine-5-carbaldehyde (0.76 g, 4.0 mmol) as a white solid. |