Hydrochloric Acid → 5-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-(methylthio)-4(5H)-thiazolone

HRID 2226436노트

반응식

HRID 2226436 반응식
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=[S:22])[NH:19][C:18]2=[O:23])[N:6]=1)([CH3:4])[CH3:3].[CH:24](N(C(C)C)CC)(C)C.CI.Cl>O1CCCC1.C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:15][C:12]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20]([S:22][CH3:24])=[N:19][C:18]2=[O:23])[N:8]=1)([CH3:13])[CH3:14]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 539399305-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone

생성물 1

HCID 539911875-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-(methylthio)-4(5H)-thiazolone수율 60%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 5-[[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-2-thioxo-4-thiazolidinone (1.00 g, 2.85 mmol) and diisopropylethylamine (0.75 g, 5.8 mmol) in tetrahydrofuran (20 mL) under nitrogen atmosphere is added methyl iodide (0.80 g, 5.6 mmol). The resulting mixture is stirred 16 hours, diluted with ethyl acetate, and with aqueous 1N hydrochloric acid solution and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 10% ethyl acetate/hexane) followed by recrystallization from ethyl acetate and hexane to give 0.62 g (60%) of the title compound, mp 205°-208° C.

후처리

  1. dry with materialThe organic phase is dried over magnesium sulfate
  2. concentrationconcentrated
  3. custompurified by flash chromatography (SiO2, 10% ethyl acetate/hexane)
  4. customfollowed by recrystallization from ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-ddec7a961424482f9604fb7e946c56a0
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05348957

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