Sodium Carbonate → 7-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(methylthio)thieno[3,2-d]pyrimidine

HRID 532467ノート

反応式

HRID 532467 の反応式
Br[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]=2[S:4][CH:3]=1.[F:13][C:14]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[F:13][C:14]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:15]=1[C:2]1[C:6]2[N:7]=[CH:8][N:9]=[C:10]([S:11][CH3:12])[C:5]=2[S:4][CH:3]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 469284277-Bromo-4-methylsulfanylthieno[3,2-d]pyrimidineHCID 682992982-(2-Fluoro-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

生成物 1

HCID 682993367-(2-Fluoro-4-methanesulfonyl-phenyl)-4-(methylthio)thieno[3,2-d]pyrimidine

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

7-bromo-4-methylsulfanylthieno[3,2-d]pyrimidine (270 mg, 1.03 mmol) was added to 1,4-dioxane (10 mL), and 2-(2-fluoro-4-methanesulfonyl-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 eq), tetrakis(triphenylphosphine)palladium(0) (71 mg, 0.06 eq), 2N aqueous sodium carbonate (3.1 mL, 3 eq) were sequentially added thereto while stirring. The reaction mixture was degassed with Ar(g), heated to 100° C., and stirred at 100° C. for 4 hours. After completion of the reaction using sodium bicarbonate, the reaction mixture was extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous magnesium sulfate, dried, and concentrated under reduced pressure to obtain a foamy residue. The residue was crystallized in the presence of diethyl ether to obtain the title compound as a yellowish solid.

後処理

  1. additionwere sequentially added
  2. customThe reaction mixture was degassed with Ar(g)
  3. stirringstirred at 100° C. for 4 hours
  4. extractionthe reaction mixture was extracted twice with ethyl acetate
  5. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a foamy residue
  9. customThe residue was crystallized in the presence of diethyl ether

出典と根拠

ORDレコード
ord-634055c2529646d3b90768c0faa5f1aa
出典データセット
uspto-grants-2014_10
特許番号
US08853213B2

反応ノート

読み込み中…