HRID2271

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1140

Toluene

C7H8

HCID14797

Potassium hydroxide

HKO

结构：Cc1ccc(-c2c(N)ncnc2OCCOc2ncc(Br)cn2)cc1

HCID11729102

未命名化合物

HCID22281976

4-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride

C11H15ClO2S

PRODUCTS

生成物

结构：CCC(C)(C)c1ccc(S(=O)(=O)Nc2ncnc(OCCOc3ccc(Br)cn3)c2-c2ccc(C)cc2)cc1

HCID19689488

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：CCCC[N+](CCCC)(CCCC)CCCC.O=S(=O)([O-])O

催化剂HCID94433

未命名化合物

溶剂HCID25517

未命名化合物

PROCEDURE

实验过程

A mixture of 6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-amine (150 mg), 4-tert-amylbenzenesulfonyl chloride (184 mg), 96% potassium hydroxide (powder, 300 mg), tetrabutylammonium hydrogen sulfate (34 mg) and toluene (10 ml) is stirred at room temperature overnight. The mixture is diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1), and recrystallized from hexane/ethyl acetate to give 4-tert-amyl-N-{6-[2-(5-bromopyridin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (188 mg).

WORKUP

后处理

extractionextracted with ethyl acetate
washThe ethyl acetate layer is washed
customdried
customevaporated
customto remove the solvent
customThe residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=5:1)
customrecrystallized from hexane/ethyl acetate

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-50229f9f65b24c3fbf8cc4093165ef6b
来源数据集: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
专利: US05728706

反应 SMILES

[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[N:17]=[CH:16][N:15]=[C:14]([NH2:18])[C:13]=2[C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)=N[CH:7]=1.[C:26]([C:31]1[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27].[OH-].[K+].[C:43]1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>[C:26]([C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH:18][C:14]2[C:13]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)=[C:12]([O:11][CH2:10][CH2:9][O:8][C:5]3[CH:43]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=3)[N:17]=[CH:16][N:15]=2)(=[O:39])=[O:38])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27]