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

HRID 2226436ノート

反応式

HRID 2226436 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ddec7a961424482f9604fb7e946c56a0
出典データセット
uspto-grants-1994_09
特許番号
US05348957

反応ノート

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