ethyl 3-(4-fluorophenyl)-3-oxopropanoate -Drug Synthesis Database

【结构式】

【分子编号】54647

【品名】ethyl 3-(4-fluorophenyl)-3-oxopropanoate

【CA登记号】

【分子式】C₁₁H₁₁FO₃

【分子量】210.2049432

【元素组成】C 62.85% H 5.27% F 9.04% O 22.83%

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：(II)

Claisen condensation of diethyl carbonate with p-fluoroacetophenone (I) produced keto ester (II). This was cyclized to the pyrimidine (IV) by treatment with acetamidine hydrochloride (III) in the presence of K2CO3 in hot EtOH. Chlorination of hydroxypyrimidine (IV) by means of POCl3 furnished the 4-chloropyrimidine (V). Finally, chloride displacement in (V) with the sodium alkoxide of 5-piperidino-1-pentanol (VI) gave rise to the target pyrimidinyl ether, which was isolated as the corresponding hydrochloride salt.

参考文献中间体

合成目标

【1】 Chokai, S.; Ukai, Y.; Aoki, T.; Ideguchi, K. (Nippon Shinyaku Co., Ltd.); Heterocyclic deriv. and medicine. EP 0781766; JP 2000136184; US 6191149; WO 9607641 .

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)	37684	1-(4-fluorophenyl)-1-ethanone	403-42-9	C₈H₇FO	详情	详情
(II)	54647	ethyl 3-(4-fluorophenyl)-3-oxopropanoate		C₁₁H₁₁FO₃	详情	详情
(III)	15866	ethanimidamide		C₂H₆N₂	详情	详情
(IV)	54648	6-(4-fluorophenyl)-2-methyl-4-pyrimidinol		C₁₁H₉FN₂O	详情	详情
(V)	54649	4-chloro-6-(4-fluorophenyl)-2-methylpyrimidine		C₁₁H₈ClFN₂	详情	详情
(VI)	54650	5-(1-piperidinyl)-1-pentanol		C₁₀H₂₁NO	详情	详情

Extended Information