HRID1082296

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID313

Hydrochloric Acid

ClH

HCID11430

Potassium Carbonate

CK2O3

HCID606665

5-Bromo-2-chloropyrimidine

C4H2BrClN2

结构：Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(O)cn2)cc1

HCID19689508

未命名化合物

PRODUCTS

生成物

结构：Cc1ccc(-c2c(NS(=O)(=O)c3ccc(C(C)(C)C)cc3)ncnc2OCCOc2ncc(Oc3ncc(Br)cn3)cn2)cc1

HCID19689499

未命名化合物

收率 92%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

CONDITIONS

反应条件

温度: 50 °C

PROCEDURE

实验过程

To a solution of 4-tert-butyl-N-{6-[2-(5-hydroxypyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (200 mg) in dimethylformamide (4 ml) is added potassium carbonate (154 mg), 5-bromo-2-chloropyrimidine (216 mg), and the mixture is stirred at 50° C. for two hours. The reaction mixture is acidified with cold hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water and brine, and dried over anhydrous sodium sulfate, and evaporated to remove the solvent. The oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=50:1), and the fractions are evaporated to remove the solvent. The resulting crude crystals are recrystallized from methylene chloride/isopropyl ether to give 4-tert-butyl-N-{6-[2-(5-(5-bromopyrimidin-2-yloxy)pyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (238 mg) as colorless needles.

WORKUP

后处理

extractionextracted with ethyl acetate
washThe organic layer is washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customevaporated
customto remove the solvent
customThe oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=50:1)
customthe fractions are evaporated
customto remove the solvent
customThe resulting crude crystals are recrystallized from methylene chloride/isopropyl ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ad40efa505874e5c8310f2b991286263
来源数据集: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05589478
来源说明: uspto-grants-1996_12

反应 SMILES

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35]([OH:38])=[CH:34][N:33]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:45][C:46]1[CH:47]=[N:48][C:49](Cl)=[N:50][CH:51]=1.Cl>CN(C)C=O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([C:21]3[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=3)=[C:19]([O:28][CH2:29][CH2:30][O:31][C:32]3[N:37]=[CH:36][C:35]([O:38][C:49]4[N:50]=[CH:51][C:46]([Br:45])=[CH:47][N:48]=4)=[CH:34][N:33]=3)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]