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CAS No. : | 1408075-48-8 | MDL No. : | MFCD23105988 |
Formula : | C7H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KFLCCZPFOPDGLN-UHFFFAOYSA-N |
M.W : | 144.17 | Pubchem ID : | 45090007 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
494 mg | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1.5h; | 70.1 Step 1. Preparation of cis-methyl 3-(6-chloropyrazolo[3,4-d]pyrimidin-1-yl)-1- methyl-cyclobutanecarboxylate. Prepared according to general procedure D using 6-chloro-1H- pyrazolo[3,4-d]pyrimidine (700 mg, 4.5 mmol), cis-methyl 3-hydroxy-1-methyl- cyclobutanecarboxylate (780 mg, 5.4 mmol), and triphenylphosphine (1.8 g, 6.8 mmol) in a solution of THF (23 mL). DIAD (1.3 mL, 6.8 mmol) added dropwise over 30 min. The reaction was stirred at rt for 1.5 h. The reaction mixture was quenched with water and brine then extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was adsorbed onto silica gel then purified silica gel chromatography (0-20% EtOAc in hexanes) to afford the title compound (494 mg). |
494 mg | With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1.5h; | 70.1 Step 1. Preparation of cis-methyl 3-(6-chloropyrazolo[3,4-d]pyrimidin-1-yl)-1- methyl-cyclobutanecarboxylate. Prepared according to general procedure D using 6-chloro-1H- pyrazolo[3,4-d]pyrimidine (700 mg, 4.5 mmol), cis-methyl 3-hydroxy-1-methyl- cyclobutanecarboxylate (780 mg, 5.4 mmol), and triphenylphosphine (1.8 g, 6.8 mmol) in a solution of THF (23 mL). DIAD (1.3 mL, 6.8 mmol) added dropwise over 30 min. The reaction was stirred at rt for 1.5 h. The reaction mixture was quenched with water and brine then extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was adsorbed onto silica gel then purified silica gel chromatography (0-20% EtOAc in hexanes) to afford the title compound (494 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 2: Cs2CO3; [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride / ethylene glycol dimethyl ether / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 2: Cs2CO3; [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride / ethylene glycol dimethyl ether / 3 h / 80 °C 3: lithium hydroxide monohydrate / methanol / 96 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / 0 - 20 °C 3: Cs2CO3; [1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride / ethylene glycol dimethyl ether / 3 h / 80 °C |
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