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【结 构 式】 
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【分子编号】58389 【品名】 【CA登记号】 |
【 分 子 式 】C5H6N2O2 【 分 子 量 】126.11492 【元素组成】C 47.62% H 4.8% N 22.21% O 25.37% |
合成路线1
该中间体在本合成路线中的序号：(VI)Condensation of the pyridyl enaminone (I) with thiourea (II) in the presence of NaOEt gives 2-mercapto-4-(pyridin-2-yl)pyrimidine (III), which is alkylated with iodomethane, producing the corresponding methylsulfanyl pyrimidine (IV). Subsequent displacement of the methylsulfanyl group of (IV) with hydrazine leads to the hydrazino pyrimidine (V). Rhodium acetate-catalyzed coupling between 3-diazo-2,4-pentanedione (VI) and 4-chlorophenol (VII) furnishes the chlorophenyl ether (VIII). The tile pyrazole derivative is finally obtained by condensation between hydrazine (V) and diketone (VIII) in the presence of p-toluenesulfonic acid in boiling EtOH.
| 【1】 Hirth, B.H.; Kane, J.L. Jr.; Janjigian, A.D.; et al.; Discovery of TNF-alpha induced apoptosis inhibitors with activity in a murine model of multiple sclerosis: Pyrazole series. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 273. |
| 【2】 Hirth, B.H.; Sneddon, S.F.; Kane, J.L.; Vinick, F.; Qiao, S.; Nahill, S.R. (Genzyme Corp.); Modulators of TNF-alpha signaling. WO 0187849 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 58385 | (E)-3-(dimethylamino)-1-(2-pyridinyl)-2-propen-1-one | C10H12N2O | 详情 | 详情 | |
| (II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (III) | 58386 | 4-(2-pyridinyl)-2-pyrimidinylhydrosulfide; 4-(2-pyridinyl)-2-pyrimidinethiol | C9H7N3S | 详情 | 详情 | |
| (IV) | 58387 | 2-(methylsulfanyl)-4-(2-pyridinyl)pyrimidine; methyl 4-(2-pyridinyl)-2-pyrimidinyl sulfide | C10H9N3S | 详情 | 详情 | |
| (V) | 58388 | 2-hydrazino-4-(2-pyridinyl)pyrimidine | C9H9N5 | 详情 | 详情 | |
| (VI) | 58389 | C5H6N2O2 | 详情 | 详情 | ||
| (VII) | 35543 | 4-chlorophenol | 106-48-9 | C6H5ClO | 详情 | 详情 |
| (VIII) | 58390 | 3-(4-chlorophenoxy)-2,4-pentanedione; 3-(4-chlorophenoxy)pentane-2,4-dione | C11H11ClO3 | 详情 | 详情 |