3-(3-chloropropyl)-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,4(1H,3H)-pyrimidinedione -Drug Synthesis Database

【结构式】

【分子编号】54369

【品名】3-(3-chloropropyl)-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【分子式】C₁₄H₂₅ClN₂O₃Si

【分子量】332.90238

【元素组成】C 50.51% H 7.57% Cl 10.65% N 8.41% O 14.42% Si 8.44%

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：(XI)

5-Methyluracil (VII) was protected with SEM-Cl (VIII) to yield the 1-SEM derivative (IX), which was subsequently alkylated with 1-bromo-3-chloropropane (X) under phase-transfer conditions to provide chloride (XI). Alkylation of piperazine (VI) with chloride (XI) in the presence of NaI and K2CO3 furnished adduct (XII). The title compound was then obtained by deprotection of (XII) upon treatment with tetrabutylammonium fluoride in THF.

参考文献中间体

合成目标

【1】 Bantle, G.W.; Elworthy, T.R.; Guzman, A.; Jaime-Figueroa, S.; Lopez-Tapia, F.J.; Morgans, D.J. Jr.; Perez-Medrano, A.; Pfister, J.R.; Sjogren, E.B.; Talamas, F.X. (F. Hoffmann-La Roche AG); Pyrimidinedione, pyrimidinetrione, triazinedione, tetrahydroquinazolinedione derivs. as alpha1-adrenergic receptor antagonists. EP 0748800; JP 1997100269 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	54367	1-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]piperazine; 5-fluoro-2-(1-piperazinyl)phenyl 2,2,2-trifluoroethyl ether		C₁₂H₁₄F₄N₂O	详情	详情
(VII)	12204	5-Methyl-2,4(1H,3H)-pyrimidinedione; Thymine	65-71-4	C₅H₆N₂O₂	详情	详情
(VIII)	27243	[2-(chloromethoxy)ethyl](trimethyl)silane	76513-69-4	C₆H₁₅ClOSi	详情	详情
(IX)	54368	5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,4(1H,3H)-pyrimidinedione		C₁₁H₂₀N₂O₃Si	详情	详情
(X)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(XI)	54369	3-(3-chloropropyl)-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,4(1H,3H)-pyrimidinedione		C₁₄H₂₅ClN₂O₃Si	详情	详情
(XII)	54370	3-(3-{4-[4-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]-1-piperazinyl}propyl)-5-methyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,4(1H,3H)-pyrimidinedione		C₂₆H₃₈F₄N₄O₄Si	详情	详情

Extended Information