Dimethyl Sulfate → 5-Bromo-3-methyl-2-(methylthio)pyrimidin-4(3H)-one

HRID 598082

Reaction equation

HRID 598082 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[OH-].[K+].[Br:10][C:11]1[C:12](=O)[NH:13][C:14]([S:17][CH3:18])=[N:15][CH:16]=1>O1CCCC1.C(OCC)(=O)C>[Br:10][C:11]1[C:7](=[O:6])[N:15]([CH3:16])[C:14]([S:17][CH3:18])=[N:13][CH:12]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 2405655-Bromo-2-(methylsulfanyl)pyrimidin-4(3H)-one

Product 1

HCID 32646665-Bromo-3-methyl-2-(methylthio)pyrimidin-4(3H)-oneYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture containing 0.70 g (5.5 mmol) of dimethyl sulfate and 0.25 g (4.5 mmol) of potassium hydroxide in 10 ml of tetrahydrofuran was added 0.5 g (2.25 mmol) of 5-Bromo-2-(methylthio)pyrimidin-4(3H)-one in portions over 15 min. After complete addition, the mixture was stirred overnight then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 20% ethyl acetate/dichloromethane gave 0.5 g (94%) of product.

Workup

  1. additionAfter complete addition
  2. washwashed with water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via Biotage chromatography
  5. washeluting with 20% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-d4e65b5a47f349258865a7eb68080063
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Linked notes

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