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CAS No. : | 809236-47-3 | MDL No. : | MFCD18074292 |
Formula : | C9H13N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 179.22 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
To a solution of <strong>[234082-35-0]methyl 3-chloro-4-fluorobenzoate</strong> (23.6 mg, 0.125 mmol) and 2-piperidin-1-ylpyrimidin-5-ol (Preparation 10, 22.4 mg 0.125 mmol) in pyridine (0.5 mL) were added cesium carbonate (122 mg, 0.375 mmol) and copper powder (16 mg, 0.25 mmol) and the reaction mixture was shaken at 120 C. for 16 hours. The reaction mixture was filtered and evaporated in vacuo. Water (1 mL) was added and the mixture extracted with EtOAc (3×1 mL). The combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was dissolved in tetrahydrofuran (0.7 mL), aqueous lithium hydroxide solution (0.7 mL of a 1M solution, 0.7 mmol) was added and the reaction shaken at 30 C. for 16 hours. The reaction was evaporated in vacuo and a 1 M aqueous solution of hydrochloric acid (0.7 mL) was added. The mixture was extracted thre times with EtOAc (3×1 mL), the combined organic layers were dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue, methanesulfonamide (11.9 mg, 0.125 mmol), DMAP (45.8 mg, 0.375 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (55 mg, 0.28 mmol) were dissolved in dichloromethane (1 mL) and shaken at 30 C. for 16 hours before evaporation in vacuo. The residue purified on a HPLC column (YMC-pack ODS-AQ 150*30 mm*5 μm, acetonitrile-water (0.1% trifluoroacetic acid) gradient) to afford the title compound (5.23 mg, 12.7 μmol).LCMS Rt=3.331 minutes MS m/z 411 [MH]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: 5-bromo-2-(piperidin-1-yl)pyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #3: With dihydrogen peroxide; acetic acid In tetrahydrofuran; hexane; water at 0℃; for 0.166667h; | 10 A solution of 5-bromo-2-piperidin-1-ylpyrimidine (1.00 g, 4.15 mmol) in freshly distilled THF (5.2 mL), was purged with argon and cooled to -78° C. To the cooled reaction mixture was added drop-wise a solution of n-butyllithium in hexane (2.5 M, 1.99 mL, 4.98 mmol). The reaction mixture was stirred at -78° C. for 10 minutes and then added dropwise over 10 minutes to a solution of trimethyl borate (0.559 mL, 4.98 mmol) in THF (5.2 mL), which had been purged with argon and cooled to 0° C. The resulting reaction mixture was stirred at 0° C. for a further 20 minutes, followed by addition of acetic acid (0.356 mL, 6.22 mmol). After a further 5 minutes of stirring, a 30% aqueous solution of hydrogen peroxide (0.517 mL, 4.57 mmol) was added dropwise and stirring continued at 0° C. for 5 minutes. A saturated aqueous solution of sodium bisulfite (50 mL) was added and the mixture extracted with EtOAc. The organic extract was washed with a saturated aqueous brine solution, dried over anhydrous sodium sulfate, filtered over Celite and concentrated in vacuo. The crude material was purified using silica gel chromatography eluting with 25% EtOAC in hexane to afford the title compound (728 mg, 98%):1H NMR (400 MHz, CDCl3): δ 1.40-1.70 (br, 6H), 3.55-3.75 (br, 4H), 8.05 (d, 2H). MS m/z 180 [MH]+, 178 [M-H]- CHN Theory-C, 60.32%, H, 7.31%, N, 23.45%CHN Found-C, 60.32%; H, 7.43%; N, 23.10%. |