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

HRID 532467노트

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HRID 532467 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-634055c2529646d3b90768c0faa5f1aa
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853213B2

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