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

HRID 2226436Notes

Reaction equation

HRID 2226436 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ddec7a961424482f9604fb7e946c56a0
Source dataset
uspto-grants-1994_09
Patent number
US05348957

Reaction notes

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