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【结 构 式】

【分子编号】62332

【品名】(2,3,5-trichlorophenyl)lithium

【CA登记号】

【 分 子 式 】C6H2Cl3Li

【 分 子 量 】187.38098

【元素组成】C 38.46% H 1.08% Cl 56.76% Li 3.7%

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)

Regioselective lithiation of 1,2,4-trichlorobenzene (V) with n-BuLi at -60 C, followed by quenching of the resultant organolithium compound (VI) with N,N-dimethylformamide yielded 2,3,5-trichlorobenzaldehyde (VII) (1), which was then reduced with NaBH4 to provide alcohol (VIII). Bromination of (VIII) using PBr3 afforded compound (IX), whose bromide atom was displaced with KCN to give the trichlorophenylacetonitrile (X). Claisen condensation of (X) with ethyl formate in the presence of NaOEt furnished the oxo nitrile sodium enolate (XI), which was subsequently O-alkylated with iodomethane yielding the methoxy acrylonitrile (XII). Finally, cyclization of (XII) with the piperazine-1-carboxamidine (IV) in EtOH gave rise to the target pyrimidine derivative

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 .
2 Patel, R.; Packham, T.W.; Germain, A.L.; Barras, J.R.; Milne, D.J. (GlaxoSmithKline plc); Process of preparing 2,3,5-trihalobenzaldehyde. WO 9507877 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 62330   C7H18N4 详情 详情
(V) 62331 1,2,4-trichlorobenzene C6H3Cl3 详情 详情
(VI) 62332 (2,3,5-trichlorophenyl)lithium C6H2Cl3Li 详情 详情
(VII) 25670 2,3,5-trichlorobenzaldehyde 56961-75-2 C7H3Cl3O 详情 详情
(VIII) 25671 (2,3,5-trichlorophenyl)methanol C7H5Cl3O 详情 详情
(IX) 25672 1-(bromomethyl)-2,3,5-trichlorobenzene C7H4BrCl3 详情 详情
(X) 25673 2-(2,3,5-trichlorophenyl)acetonitrile C8H4Cl3N 详情 详情
(XI) 62333 sodium (Z)-2-cyano-2-(2,3,5-trichlorophenyl)-1-ethenolate C9H3Cl3NNaO 详情 详情
(XII) 62334 (E)-3-methoxy-2-(2,3,5-trichlorophenyl)-2-propenenitrile C10H6Cl3NO 详情 详情
Extended Information