2,4-dichloro-6-ethyl-5-fluoropyrimidine -Drug Synthesis Database

【结构式】

【分子编号】45724

【品名】2,4-dichloro-6-ethyl-5-fluoropyrimidine

【CA登记号】

【分子式】C₆H₅Cl₂FN₂

【分子量】195.0229832

【元素组成】C 36.95% H 2.58% Cl 36.36% F 9.74% N 14.36%

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：(XII)

Alternatively, 6-ethyl-5-fluoropyrimidin-4-ol (IV) can be obtained by reaction of 2,4-dichloro-5-fluoropyrimidine (X) with ethylmagnesium bromide in THF to give the dihydropyrimidine derivative (XI), which is aromatized by reaction with I2 and TEA in THF yielding 2,4-dichloro-6-ethyl-5-fluoropyrimidine (XII). The reaction of (XII) with NaOH and NH4Cl affords the aminooxy derivative (XIII) which is finally submitted to a reductive dechlorination and deamination with H2 over Pd/C in ethanol/water.

参考文献中间体

合成目标

【1】 Butters, M.; et al.; Process development of voriconazole: A novel broad-spectrum triazole antifungal agent. Org Process Res Dev 2001, 5, 1, 28.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(IV)	45720	6-ethyl-5-fluoro-4-pyrimidinol	C₆H₇FN₂O	详情	详情
(X)	45722	2,4-dichloro-5-fluoropyrimidine；2,4-Dichloro-5-fluorouracil	C₄HCl₂FN₂	详情	详情
(XI)	45723	bromo[2,4-dichloro-6-ethyl-5-fluoro-1(6H)-pyrimidinyl]magnesium	C₆H₆BrCl₂FMgN₂	详情	详情
(XII)	45724	2,4-dichloro-6-ethyl-5-fluoropyrimidine	C₆H₅Cl₂FN₂	详情	详情
(XIII)	45725	4-(aminooxy)-2-chloro-6-ethyl-5-fluoropyrimidine; O-(2-chloro-6-ethyl-5-fluoro-4-pyrimidinyl)hydroxylamine	C₆H₇ClFN₃O	详情	详情

Extended Information