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

HRID 598083

反応式

HRID 598083 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-09b6f055567547c3b2024293cd61e501
出典データセット
uspto-grants-2011_03
特許番号
US07897607B2

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