6-[1-(2,6-difluorophenyl)ethyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone -Drug Synthesis Database

【结构式】

【分子编号】51831

【品名】6-[1-(2,6-difluorophenyl)ethyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone

【CA登记号】

【分子式】C₁₂H₁₀F₂N₂OS

【分子量】268.2870864

【元素组成】C 53.72% H 3.76% F 14.16% N 10.44% O 5.96% S 11.95%

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：(VI)

The methylation of 2-(2,6-difluorophenyl)acetic acid (I) with Me-Cl and LDA in THF/HMPA gives 2-(2,6-difluorophenyl)propionic acid (II), which is condensed with malonic acid monoethyl ester potassium salt (III) to yield 4´(2,6-difluorophenyl)-3-oxopentanoic acid (IV). The cyclization of (IV) with thiourea (V) affords 6-[1-(2,6-difluorophenyl)ethyl]-2-thioxo-1,2,3,4-tetrahydropyrimidin-4-one (VI), which is finally alkylated with cyclopentyl chloride (VII) to provide the target pyrimidinone derivative.

参考文献中间体

合成目标

【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159.

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)	51809	2,6-Difluorophenylacetic acid	85068-28-6	C₈H₆F₂O₂	详情	详情
(II)	51820	2-(2,6-difluorophenyl)propionic acid		C₉H₈F₂O₂	详情	详情
(III)	14338	potassium 3-ethoxy-3-oxopropanoate	6148-64-7	C₅H₇KO₄	详情	详情
(IV)	51830	ethyl 4-(2,6-difluorophenyl)-3-oxopentanoate		C₁₃H₁₄F₂O₃	详情	详情
(V)	10180	Thiourea	62-56-6	CH₄N₂S	详情	详情
(VI)	51831	6-[1-(2,6-difluorophenyl)ethyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone		C₁₂H₁₀F₂N₂OS	详情	详情
(VII)	51794	1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride	930-28-9	C₅H₉Cl	详情	详情

Extended Information