Water → 5-(2,4-Dimethylphenyl)-3-methyl-2-(methylthio)pyrimidin-4(3H)-one

HRID 598083

반응식

HRID 598083 반응식
Br[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][C:13]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:14]=1[C:2]1[C:3](=[O:11])[N:4]([CH3:10])[C:5]([S:8][CH3:9])=[N:6][CH:7]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 32646665-Bromo-3-methyl-2-(methylthio)pyrimidin-4(3H)-oneHCID 4198739(2,4-Dimethylphenyl)boronic acid

생성물 1

HCID 589385625-(2,4-Dimethylphenyl)-3-methyl-2-(methylthio)pyrimidin-4(3H)-one수율 86%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

A mixture containing 0.2 g (0.84 mmol) of 5-bromo-3-methyl-2-(methylthio)pyrimidin-4(3H)-one, 0.19 g (1.3 mmol) of 2,4-dimethylphenyl boronic acid, 0.35 g (2.5 mmol) of potassium carbonate, 0.15 ml (8.4 mmol) of water, and 0.25 g (0.21 mmol) of tetrakis(triphenylphosphine)palladium(0) in 10 ml of dioxane was heated to 90° C. under a nitrogen atmosphere overnight. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 30% ethyl acetate/hexanes gave 0.18 g (86%) of product.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with saturated sodium bicarbonate
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationFiltration, removal of solvent and purification of the residue via biotage
  5. washeluting with 30% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-09b6f055567547c3b2024293cd61e501
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897607B2

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