【结 构 式】 |
【分子编号】35393 【品名】5-(2-methylphenyl)-1,2,3,6-tetrahydropyridine 【CA登记号】 |
【 分 子 式 】C12H15N 【 分 子 量 】173.25784 【元素组成】C 83.19% H 8.73% N 8.08% |
合成路线1
该中间体在本合成路线中的序号:(IV)The Grignard reaction of 1-(tert-butoxycarbonyl)piperidin-3-one (I) with 2-methylphenylmagnesium bromide (II) in THF gives the tertiary alcohol (III), which is dehydrated with TFA or HCl in dioxane yielding the tetrahydropyridine (IV). The condensation of (IV) with 2,4-dichloro-6-methylpyrimidine (V) by means of DIEA in ethanol affords 2-chloro-6-methyl-4-[3-(2-methylphenyl)-1,2,3,6-tetrahydropyridin-1-yl]pyrimidine (VI), which is further condensed with 4-isopropyl-2-(methylsulfanyl)aniline (VII) by means of DIEA in refluxing ethylene glycol to give the secondary amine (VIII). Finally, this compound is alkylated with ethyl iodide and NaH in DMF.
【1】 Chaki, S.; Nakazato, A.; Okubo, T.; Kumagai, T.; Tomisawa, K.; Okuyama, S.; CRF1 receptor antagonists: Aryl-1,2,3,6-tetrahydropyridinopyrimidine derivatives. Symp Med Chem 1998, Abst 1-P-26. |
【2】 Okubo, T.; Okuyama, S.; Nakazato, A.; Tomisawa, K.; Aibe, I.; Chaki, S.; Kumagai, T.; Tanaka, H. (Taisho Pharmaceutical Co., Ltd.); 4-Tetrahydropyridylpyrimidine derivs.. EP 0976745; JP 1999228568; WO 9842699 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
10925 | Iodoethane;ethyl iod | 75-03-6 | C2H5I | 详情 | 详情 | |
(I) | 18620 | tert-butyl 4-oxo-1-piperidinecarboxylate;BOC-Piperidone;N-(tert-Butoxycarbonyl)-4-piperidone; N-Boc-4-piperidone | 79099-07-3 | C10H17NO3 | 详情 | 详情 |
(II) | 35391 | bromo(2-methylphenyl)magnesium | C7H7BrMg | 详情 | 详情 | |
(III) | 35392 | tert-butyl 3-hydroxy-3-(2-methylphenyl)-1-piperidinecarboxylate | C17H25NO3 | 详情 | 详情 | |
(IV) | 35393 | 5-(2-methylphenyl)-1,2,3,6-tetrahydropyridine | C12H15N | 详情 | 详情 | |
(V) | 35387 | 2,4-dichloro-6-methylpyrimidine | 5424-21-5 | C5H4Cl2N2 | 详情 | 详情 |
(VI) | 35394 | 2-chloro-4-methyl-6-[5-(2-methylphenyl)-3,6-dihydro-1(2H)-pyridinyl]pyrimidine | C17H18ClN3 | 详情 | 详情 | |
(VII) | 35389 | 4-isopropyl-2-(methylsulfanyl)phenylamine; 4-isopropyl-2-(methylsulfanyl)aniline | C10H15NS | 详情 | 详情 | |
(VIII) | 35395 | N-[4-isopropyl-2-(methylsulfanyl)phenyl]-4-methyl-6-[5-(2-methylphenyl)-3,6-dihydro-1(2H)-pyridinyl]-2-pyrimidinamine; N-[4-isopropyl-2-(methylsulfanyl)phenyl]-N-[4-methyl-6-[5-(2-methylphenyl)-3,6-dihydro-1(2H)-pyridinyl]-2-pyrimidinyl]amine | C27H32N4S | 详情 | 详情 |