1-[(Z)-5-chloro-4-penten-2-ynyl]-3-(2-propynyl)-2,4(1H,3H)-pyrimidinedione -Drug Synthesis Database

【结构式】

【分子编号】60463

【品名】1-[(Z)-5-chloro-4-penten-2-ynyl]-3-(2-propynyl)-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【分子式】C₁₂H₉ClN₂O₂

【分子量】248.66844

【元素组成】C 57.96% H 3.65% Cl 14.26% N 11.27% O 12.87%

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)

Alkylation of uracil (I) with propargyl bromide (II) in the presence of DBU affords the N1-alkylated product (III). Palladium-catalyzed coupling of the terminal alkyne (III) with cis-1,2-dichloroethene (IV) furnishes the chlorovinyl adduct (V). Subsequent alkylation at the N3-position of (V) with propargyl bromide (II) and DBU leads to the open-chain enediyne (VI). This is finally cyclized to the target bicyclic compound in the presence of Pd(PPh3)4, CuI and butylamine.

参考文献中间体

合成目标

【1】 Hakimelahi, G.H.; et al.; A novel approach towards studying non-genotoxic enediynes as potential anticancer therapeutics. Bioorg Med Chem 2002, 10, 5, 1321.

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)	30921	2,4(1H,3H)-pyrimidinedione; Uracil	66-22-8	C₄H₄N₂O₂	详情	详情
(II)	11176	3-Bromopropyne; 3-Bromo-1-propyne	106-96-7	C₃H₃Br	详情	详情
(III)	60461	1-(2-propynyl)-2,4(1H,3H)-pyrimidinedione		C₇H₆N₂O₂	详情	详情
(IV)	28793	(Z)-1,2-dichloroethene	156-59-2	C₂H₂Cl₂	详情	详情
(V)	60462	1-[(Z)-5-chloro-4-penten-2-ynyl]-2,4(1H,3H)-pyrimidinedione		C₉H₇ClN₂O₂	详情	详情
(VI)	60463	1-[(Z)-5-chloro-4-penten-2-ynyl]-3-(2-propynyl)-2,4(1H,3H)-pyrimidinedione		C₁₂H₉ClN₂O₂	详情	详情

Extended Information