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【结 构 式】 
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【分子编号】68142 【品名】6-bromo-8-cyclopentyl-5-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one 【CA登记号】 |
【 分 子 式 】C14H16BrN3OS 【 分 子 量 】354.271 【元素组成】C 47.46% H 4.55% Br 22.55% N 11.86% O 4.52% S 9.05% |
合成路线1
该中间体在本合成路线中的序号：(I)Treatment of 6-bromo-8-cyclopentyl-5-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (I) with 2-benzenesulfonyl-3-phenyl-oxaziridine (II) in CH2Cl2 results in the corresponding sulfoxide (III) . Subsequent displacement of the methylsulfinyl group of compound (III) with 2-amino-5-(4-Boc-1-piperazinyl)pyridine (IV) in boiling toluene provides the diarylamine adduct (V), which is subjected to Stille coupling with (ethoxyvinyl)tributylstannane (VI) in the presence of Pd(PPh3)4 to give the ethoxyvinyl derivative (VII). Finally, compound (VII) is submitted to simultaneous enol ether hydrolysis and cleavage of the Boc-protecting group by means of HCl in CH2Cl2 .
| 【1】 Toogood, P.L., Harvey, P.J., Repine, J.T. et al. Discovery of a potent and selective inhibitor of cyclin-dependent kinase 4/6. J Med Chem 2005, 48(7): 2388-406. |
| 【2】 Barvian, M.R., Quin, J. III, Sheehan, D.J. et al. (Pfizer Inc.). 2-(Pyridin-2-ylamino)-pyrido[2,3-d]pyrimidin-7-ones. EP 1470124, JP 2005519909, US 2003149001, US 6936612, WO 2003062236. |
| 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) | 68142 | 6-bromo-8-cyclopentyl-5-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one | C14H16BrN3OS | 详情 | 详情 | |
| (II) | 31834 | 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine;2-(Phenylsulfonyl)-3-phenyloxaziridine;2-Benzenesulfonyl-3-phenyloxaziridine;3-Phenyl-2-phenylsulfonyloxaziridine;3-Phenyl-N-phenylsulfonyloxaziridine;N-(Phenylsulfonyl)phenyloxaziridine;N-Benzenesulfonyl-3-phenyloxaziridine | 63160-13-4 | C13H11NO3S | 详情 | 详情 |
| (III) | 68143 | 6-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one | C14H16BrN3O2S | 详情 | 详情 | |
| (IV) | 68144 | tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate | C14H22N4O2 | 详情 | 详情 | |
| (V) | 68145 | tert-butyl 4-(6-((6-bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate | C27H34BrN7O3 | 详情 | 详情 | |
| (VI) | 19760 | ethyl 1-(tributylstannyl)vinyl ether; tributyl(1-ethoxyvinyl)stannane | 97674-02-7 | C16H34OSn | 详情 | 详情 |
| (VII) | 61701 | tert-butyl 4-(6-((8-cyclopentyl-6-(1-ethoxyvinyl)-5-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate | C31H41N7O4 | 详情 | 详情 |