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

HRID 598082

반응식

HRID 598082 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4e65b5a47f349258865a7eb68080063
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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