* 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.
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18.0h;
Diisopropyl diazocarboxylate (292 mg, 1.45 mmol) was added to a solution of 3- bromo-5-methylphenol (200 mg, 0.964 mmol), oxetan-3-ol (89 mg, 1.2 mmol) and triphenylphosphine (379 mg, 1.45 mmol) in THF (4.2 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (10percent) to give the title compound (218 mg, 0.827 mmol, 86percent) as a colorless oil
86%
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18.0h;
Diisopropyl diazocarboxylate (292 mg, 1.45 mmol) was added to a solution of 3- bromo-5-methylphenol (200 mg, 0.964 mmol), oxetan-3-ol (89 mg, 1.2 mmol) and triphenylphosphine (379 mg, 1.45 mmol) in THF (4.2 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1 N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (10percent) to give the title compound (218 mg, 0.827 mmol, 86percent) as a colorless oil.
1,3-dimethyl-5-[(oxetan-3-yloxy)methyl]-1H-pyrazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
69%
To a solution of oxetan-3-ol (0.273 mL, 4.14 mmol) in dry DMF (5 mL) was added sodium hydride (60% in mineral oil, 265.5 mg, 5.53 mmol), and the mixture was stirred at r.t. for about 1 h. 5-(Chloromethyl)-l,3-dimethyl-lH-pyrazole (400 mg, 2.76 mmol) in DMF (5 mL) was added and the reaction mixture was stirred for 16 h at r.t. After removal of DMF under vacuum, the residue was dissolved in DCM (50 mL) and water (20 mL). The aqueous layer was extracted with DCM and the combined organic extracts were washed with brine, then dried over Na2S04 and evaporated to dryness. The crude residue was purified by column chromatography, with a gradient of 25-100%) EtOAc in heptane, to afford the title compound (349 mg, 69%). Method B HPLC-MS: MH+ mlz 183, RT 1.09 minutes (100%)
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 18h;
Diisopropyl diazocarboxylate (292 mg, 1.45 mmol) was added to a solution of 2- bromo-5-chlorophenol (200 mg, 0.964 mmol), oxetan-3-ol (89 mg, 1.2 mmol) andtriphenylphosphine (379 mg, 1.45 mmol) in THF (4.2 mL). The reaction mixture was stirred at r.t. for 18 h. Ethyl acetate was added and the mixture was washed with 1 N NaOH (3x). The organic layer was dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (10%) to give the title compound (208 mg, 0.789 mmol, 82%).
N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]-4-(oxetanyl-3-yloxymethyl)benzamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
4 mg
With sodium carbonate; In acetonitrile; at 100℃; for 1h;Microwave irradiation;
To the reaction flask was added 4-chloromethyl-N-[4-methyl-3-(4-pyridin-3-yl-pyrimidin-2-ylamino)phenyl]benzamide (60 mg), Na2CO3 (250mg), acetonitrile (10ml) and 3-hydroxyoxetane (50 mg). the reaction was heated in a microwave at 100C for 1 hour, and the product was subjected to preparative HPLC to give Compound 6 (4 mg).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
