With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
Cesium carbonate 288 mg (0.884 mmol) and 2-(3-bromopropoxy)tetrahydropyran 0.120 mL (0.708 mmol) were added to a DMF (4 mL) solution of 1-(5-bromopyrimidin-2-yl)piperidin-4-one oxime 120 mg (0.443 mmol) synthesized in the same manner as in Reference Example 66, and the mixture was stirred at 80C for 9 hours. After the completion of the reaction, water was added to the reaction mixture, and followed by extraction with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (eluting solvent: hexane:ethyl acetate) to give the title compound 143 mg (0.346 mmol, yield 78%) as a colorless oil. Mass spectrum (CI, m/z):413, 415[M+1]+. 1H-NMR spectrum (400MHz, DMSO-d6) delta:8.48 (s, 2H), 4.59 – 4.49 (m, 1H), 4.08 – 3.98 (m, 2H), 3.88 – 3.60 (m, 6H), 3.48 – 3.36 (m, 2H), 2.58 – 2.50 (m, 2H), 2.38 – 2.30 (m, 2H), 1.93 – 1.77 (m, 2H), 1.75 – 1.32 (m, 6H).
As the paragraph descriping shows that 33821-94-2 is playing an increasingly important role.
Reference£º
Patent; UBE Industries, Ltd.; KOMORI, Ken-ichi; NINOMIYA, Akishi; USHIYAMA, Shigeru; SHINOHARA, Masaru; ITO, Koji; KAWAGUCHI, Tetsuo; TOKUNAGA, Yasunori; KAWADA, Hiroyoshi; YAMADA, Haruka; SHIRAISHI, Yusuke; KOJIMA, Masahiro; ITO, Masaaki; KIMURA, Tomio; (432 pag.)EP3333163; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics