HRID1082286

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID25517

未命名化合物

HCID4311764

Sodium borohydride (Na(BH4))

H4BNa

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

HCID11028007

未命名化合物

PRODUCTS

生成物

HCID10962637

未命名化合物

收率 66.9%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID22597222

未命名化合物

PROCEDURE

实验过程

To a solution of 4-tert-butyl-N-[6-{2-(5-formylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (143 mg) in tetrahydrofuran-isopropanol (4 ml-4 ml) is added sodium borohydride (13 mg) under ice-cooling, and the mixture is reacted for two hours. The mixture is treated with 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/methanol=200:1~50:1), and crystallized from diethyl ether to give 4-tert-butyl-N-[6-{2-(5-hydroxymethylpyrimidin-2-yloxy)ethoxy}-5-(4-methylphenyl)pyrimidin-4-yl]benzenesulfonamide (96 mg).

WORKUP

后处理

temperaturecooling
customthe mixture is reacted for two hours
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/methanol=200:1~50:1)
customcrystallized from diethyl ether

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-3d18108b855e4dc5ba8da6ac289909cd
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]([CH:38]=[O:39])=[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].[BH4-].[Na+].[Cl-].[NH4+]>O1CCCC1.C(O)(C)C>[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]([CH2:38][OH:39])=[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]