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【结 构 式】

【分子编号】25676

【品名】(E)-4,4-diethoxy-3-methoxy-2-(2,3,5-trichlorophenyl)-2-butenenitrile

【CA登记号】

【 分 子 式 】C15H16Cl3NO3

【 分 子 量 】364.65508

【元素组成】C 49.41% H 4.42% Cl 29.17% N 3.84% O 13.16%

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:(VII)

2,3,5-Trichlorobenzaldehyde (I) was reduced with NaBH4 to the benzyl alcohol (II) and then converted to the corresponding bromide (III) by means of PBr3 in benzene. Displacement of bromide group of (III) with KCN gave 2,3,5-trichlorophenylacetonitrile (IV), which was condensed with ethyl diethoxyacetate (V) in the presence of NaOEt to provide keto nitrile (VI). Subsequent treatment of (VI) with ethereal diazomethane generated the enol ether (VII). This was cyclized with guanidine (VIII) in boiling EtOH to produce pyrimidine (IX). After ketal hydrolysis of (IX), the resulting aldehyde (X) was reduced with NaBH4 to alcohol (XI). Finally, treatment of (XI) with diethylaminosulfur trifluoride in cold CH2Cl2 provided the desired fluoromethyl compound.

1 Miller, A.A.; Nobbs, M.S.; Hyde, R.M.; Leach, M.J. (Glaxo Wellcome plc); Pharmacologically active CNS cpds.. AU 8945964; EP 0372934; EP 0713703; EP 0715851; EP 0727212; EP 0727213; EP 0727214; JP 1990202876; US 5587380; US 5597828; US 5635507; US 5684005 .
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) 25670 2,3,5-trichlorobenzaldehyde 56961-75-2 C7H3Cl3O 详情 详情
(II) 25671 (2,3,5-trichlorophenyl)methanol C7H5Cl3O 详情 详情
(III) 25672 1-(bromomethyl)-2,3,5-trichlorobenzene C7H4BrCl3 详情 详情
(IV) 25673 2-(2,3,5-trichlorophenyl)acetonitrile C8H4Cl3N 详情 详情
(V) 25674 ethyl 2,2-diethoxyacetate 6065-82-3 C8H16O4 详情 详情
(VI) 25675 4,4-diethoxy-3-oxo-2-(2,3,5-trichlorophenyl)butanenitrile C14H14Cl3NO3 详情 详情
(VII) 25676 (E)-4,4-diethoxy-3-methoxy-2-(2,3,5-trichlorophenyl)-2-butenenitrile C15H16Cl3NO3 详情 详情
(VIII) 14790 Guanidine 113-00-8 CH5N3 详情 详情
(IX) 25677 2-amino-6-(diethoxymethyl)-5-(2,3,5-trichlorophenyl)-4-pyrimidinylamine C15H17Cl3N4O2 详情 详情
(X) 25678 2,6-diamino-5-(2,3,5-trichlorophenyl)-4-pyrimidinecarbaldehyde C11H7Cl3N4O 详情 详情
(XI) 25679 [2,6-diamino-5-(2,3,5-trichlorophenyl)-4-pyrimidinyl]methanol C11H9Cl3N4O 详情 详情
Extended Information