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Chemical Structure| 1314391-51-9 Chemical Structure| 1314391-51-9

Structure of 1314391-51-9

Chemical Structure| 1314391-51-9

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Product Details of [ 1314391-51-9 ]

CAS No. :1314391-51-9
Formula : C15H22ClN3O3
M.W : 327.81
SMILES Code : ClC(N=C1)=NC=C1OCC(CC2)CCN2C(OC(C)(C)C)=O
MDL No. :MFCD28403741

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Application In Synthesis of [ 1314391-51-9 ]

* 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 [ 1314391-51-9 ]

[ 1314391-51-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 161975-39-9 ]
  • [ 4983-28-2 ]
  • [ 1314391-51-9 ]
YieldReaction ConditionsOperation in experiment
95.05% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h;Inert atmosphere; Under nitrogen atmosphere, potassium carbonate (74.12 g, 536.28 mmol) was added into a solution of intermediate 7A (94.40 g, 321.77 mmol) and <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (35.00 g, 268.14 mmol) in DMF (1.00 L). The reaction solution was left at 80 C. for 16 hours, and thin layer chromatography was used to detect the completion of the reaction. Then the reaction solution was cooled to room temperature and concentrated, then water (500 mL) was added into the residue and extracted with ethyl acetate (300 mL*3). The organic phase was washed with brine (400 mL*2) and dried over anhydrous sodium sulfate, then filtered and concentrated. Then the residue was purified by column chromatography to give the intermediate 7B (pale yellow solid, 84.00 g, 95.05% yield). LCMS (ESI) m/z: 327.7 (M+1). 1HNMR (400 MHz, DMSO-d6) delta ppm 1.08-1.25 (m, 2H) 1.40 (s, 9H) 1.69-1.78 (m, 2H) 1.88-2.03 (m, 1H) 2.58-2.88 (m, 2H) 3.89-4.05 (m, 4H) 8.50-8.57 (m, 2H)
94% With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 5h; tert-Butyl 4-((methylsulfonyloxy)methyl)piperidin-l-carboxylate (Step 2 of Intermediate 1, 2.00 g, 6.82 mmol) was dissolved in DMF (80 mL). K2C03 (3.33 g, 10.23 mmol) was added thereto, followed by stirring for 5 minutes. 2-Chloropyrimidin-5-ol (890 mg, 6.82 mmol) was added thereto, followed by stirring at 80 C for 5h. To the reaction mixture, water was added, and the mixture was extracted with EtOAc. The organic layer was washed with saturated NH4C1 aqueous solution, dried with anhydrous MgS04, and then concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (EtOAc hexane = 30 % ~ 70 %) to obtain white solid (2.10 g, 94%).
94% t-butyl 4-((methylsulfonyloxy)methyl)piperidin-1-carboxylate (the product of synthesis step 2 of compound 431; 2.00 g, 6.82 mmol) was dissolved in DMF (80 mL). K2CO3 (3.33 g, 10.23 mmol) was added thereto, and stirred for 5 minutes. <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (890 mg, 6.82 mmol) was added thereto, following with stirring at 80 C. for 5 hours. The reaction mixture was added with water, and extracted with EtOAc. The organic layer was washed with saturated NH4Cl aqueous solution, dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography (EtOAchexane=30%?70%) to yield the title compound as white solid (2.10 g, 94%)
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; To a solution of 4-methanesulfonyloxymethylpiperidine-l-carboxylic acid tert-butyl ester (Preparation 23, 1.47g, 5.0mmol) and <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (0.65g, 5.0mmol) in DMF (80mL) was added potassium carbonate (0.83g, 6.0mmol) and the reaction was heated to 80C until complete. The solvent was removed in vacuo, and the resulting residue was re- dissolved in EtOAc (300mL). The solution was washed with 1M NaOH solution (200mL), brine (200mL), then dried (MgS04) and the solvent was removed in vacuo. Purification by column chromatography (IH:EtOAc, 70:30) afforded the title compound: lH NMR delta?(400MHz, CDCI3): 8.30 (s, 1H), 4.18 (br. s., 2H), 3.92 (dd, J=6.25, 3.51 Hz, 2H), 2.78 (t, J=12.30 Hz, 2H), 2.09 - 1.95 (m, 1H), 1.84 (d, J=12.89 Hz, 2H), 1.49 (s, 9H), 1.41 - 1.24 (m,2H).

  • 2
  • [ 158407-04-6 ]
  • [ 4983-28-2 ]
  • [ 1314391-51-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In N,N-dimethyl-formamide; at 60℃; for 24h; To a pressure vial equipped with a stir bar was added rt-butyl 4- (bromomethyl)piperidine-1-carboxylate (4.95 g, 17.8 mmol), <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong>(Intermediate No.86 Step 2, 2.3 g, 17.8 mmol) and DMF (59 mL). Sodium hydride (60 wtpercent, 0.47 g, 19.6 mmol) was added and the vial was sealed and heated to 60 °C for 24 hours. The crude reaction mixture was diluted with ethyl acetate and filtered through a column pre-packed with Celite. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (MPLC, 0-50percent EtOAc-hexanes) to give tert-butyl 4-[(2-chloropyrimidin-5- y l)oxy]methyl } piperidine- 1 -carboxylate.LRMS (ESI) calc'd for CI 1H15C1N303 [M+H]+: 272, Found: 272 (carbamic acid).
  • 3
  • [ 1138820-45-7 ]
  • [ 4983-28-2 ]
  • [ 1314391-51-9 ]
YieldReaction ConditionsOperation in experiment
31.7% With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 16h; A suspension of tert-butyl 4-(((trifluoromethylsulfonyl)oxy)piperidine-1-carboxylate (6.2 g, 21.1 mmol), <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (2.5 g, 19.2 mmol) and potassium carbonate ( 13.3 g, 96 mmol) in dimethylsulfoxide (100 mL) was stirred at llOoC for 16 hours. The reaction mixture was cooled to room temperature and dimethylsulfoxide was distilled off under reduced pressure. The residue was then treated with water (50 mL) and precipitate was formed, filtered off and purified by column chromatography eluting with hexanes: ethyl acetate mixture (3:2) by volume to afford the title compound (2.0 g, 31.7 %) as a white crystalline powder:
31.7% With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 16h; [0545] A suspension of tert-butyl 4-(((trifluoromethylsulfonyl)oxy)piperidine-1-carboxylate (6.2 g, 21.1 mmol), <strong>[4983-28-2]2-chloropyrimidin-5-ol</strong> (2.5 g, 19.2 mmol) and potassium carbonate (13.3 g, 96 mmol) in dimethylsulfoxide (100 mL) was stirred at 110 for 16 hours. The reaction mixture was cooled to room temperature and dimethylsulfoxide was distilled off under reduced pressure. The residue was then treated with water (50 mL) and precipitate was formed, filtered off and purified by column chromatography eluting with hexanes: ethyl acetate mixture (3:2) by volume to afford the title compound (2.0 g, 31.7 %) as a white crystalline powder: 1H NMR (400 MHz, DMSO-d6) delta 8.53 (s, 2H), 4.02 (d, J = 6.4 Hz, 2H), 3.96 (d, J = 12.4 Hz, 2H), 3.24- 3.23 (m, 1H), 2.74 (s, 2H), 2.02- 1.85 (m, 1H), 1.73 (d, J = 11.1Hz, 2H), 1.39 (s, 9H), 1.24- 1.02 (m, 2H).
  • 4
  • [ 123855-51-6 ]
  • [ 4983-28-2 ]
  • [ 1314391-51-9 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h;Inert atmosphere; General procedure: Compound 3-(dimethylamino)propan-1-ol (825.28 mg, 8 mmol) and triphenylphosphine (2.517 g, 9.6mmol) were added successively to a suspension of 19 (1.044 g, 8 mmol) in THF (15 mL) under nitrogen.A solution of DIAD (1.67 g, 9.6 mmol) in THF (2 mL) was then slowly added dropwise with ice cooling.The resultant solution was stirred at room temperature for 12 hours. The aqueous phase wasextracted with dichloromethane (40 mL 3). The combined organic layer was washed with H2O (40 mL)and brine (20 mL), and then dried over anhydrous Na2SO4, filtered and evaporated in vacuo. Theresidue was purified by flash chromatography over silica gel (DCM/MeOH = 40:110:1) to give 20a.
 

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