Hydrochloric Acid → 4-[2-(5-bromopyrimidin-2-yloxy)-1,1-dimethylethyl]-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

HRID 2299

반응식

HRID 2299 반응식
[H-].[Na+].[OH:3][CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]2[C:23]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:22]([O:31][CH2:32][CH2:33][OH:34])[N:21]=[CH:20][N:19]=2)(=[O:16])=[O:15])=[CH:10][CH:9]=1)([CH3:7])[CH3:6].[Br:35][C:36]1[CH:37]=[N:38][C:39](Cl)=[N:40][CH:41]=1.Cl>CC(N(C)C)=O.O1CCCC1>[Br:35][C:36]1[CH:37]=[N:38][C:39]([O:3][CH2:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C:18]3[C:23]([C:24]4[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=4)=[C:22]([O:31][CH2:32][CH2:33][O:34][C:39]4[N:40]=[CH:41][C:36]([Br:35])=[CH:37][N:38]=4)[N:21]=[CH:20][N:19]=3)(=[O:15])=[O:16])=[CH:10][CH:9]=2)([CH3:7])[CH3:6])=[N:40][CH:41]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidineHCID 196895154-(2-hydroxy-1,1-dimethylethyl)-N-{6-[2-hydroxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide

생성물 1

HCID 196895184-[2-(5-bromopyrimidin-2-yloxy)-1,1-dimethylethyl]-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide수율 33.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 31374Dimethylacetamide용매2회

실험 절차

To a suspension of sodium hydride (65 mg) in dimethylacetamide (0.5 ml) and tetrahydrofuran (0.5 ml) is added dropwise a solution of 4-(2-hydroxy-1,1-dimethylethyl)-N-{6-[2-hydroxyethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (135 mg) in dimethylacetamide (2 ml) and THF (2 ml) solution over period of 5 minutes at room temperature, and thereto is added 5-bromo-2-chloropyrimidine (399 mg). The mixture is stirred at room temperature for 6 days. The reaction mixture is acidified with cold diluted hydrochloric acid, and extracted with ethyl acetate. The organic layer is washed with water and saturated brine, 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=100:1), and evaporated to remove the solvent. The resulting crude crystals are recrystallized from methylene chloride/isopropyl ether to give 4-[2-(5-bromopyrimidin-2-yloxy)-1,1-dimethylethyl]-N-{6-[2-(5-bromopyrimidin-2-yloxy)ethoxy]-5-(4-methylphenyl)pyrimidin-4-yl}benzenesulfonamide (77 mg) as colorless crystals.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customto remove the solvent
  6. customThe oily residue is purified by silica gel column chromatography (solvent; chloroform/ethyl acetate=100:1)
  7. customevaporated
  8. customto remove the solvent
  9. customThe resulting crude crystals are recrystallized from methylene chloride/isopropyl ether

출처 및 근거

ORD 기록
ord-d5b502a9c1d04da5bcd8e0a9c3285742
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728706

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