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【结 构 式】

【分子编号】61701

【品名】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

【CA登记号】

【 分 子 式 】C31H41N7O4

【 分 子 量 】575.711

【元素组成】C 64.67% H 7.18% O 17.03% O 11.12%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

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
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