Sodium hydride → 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyrimidin-2-yloxy)ethylamino}pyrimidin-4-yl]benzenesulfonamide

HRID 1082263

반응식

HRID 1082263 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([NH:30][CH2:31][CH2:32][OH:33])[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[C:37]1[N:42]=[CH:41][CH:40]=[CH:39][N:38]=1.[Cl-].[NH4+]>CC(N(C)C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[CH:23]=3)=[C:19]([NH:30][CH2:31][CH2:32][O:33][C:37]3[N:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:18]=[CH:17][N:16]=2)(=[O:12])=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 744042-ChloropyrimidineHCID 196894744-tert-butyl-N-{6-(2-hydroxyethylamino)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

생성물 1

HCID 110061474-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyrimidin-2-yloxy)ethylamino}pyrimidin-4-yl]benzenesulfonamide수율 92.5%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

To a solution of Compound B (116 mg) obtained in Example 19-(1) in dimethylacetamide (2 ml) is added sodium hydride (60% dispersion-type, 33 mg), and thereto is added 2-chloropyrimidine (40 mg). The reaction solution is stirred at room temperature overnight, and the mixture is treated 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/methanol=20:1), and crystallized from chloroform/diisopropyl ether to give 4-tert-butyl-N-[5-(3-methoxyphenoxy)-6-{2-(pyrimidin-2-yloxy)ethylamino}pyrimidin-4-yl]benzenesulfonamide (125 mg) as crystals.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=20:1)
  7. customcrystallized from chloroform/diisopropyl ether

출처 및 근거

ORD 기록
ord-957fbe9d212c4e0a9b1bbf000d89c23a
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05589478

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