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

HRID 532467Notes

Reaction equation

HRID 532467 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-634055c2529646d3b90768c0faa5f1aa
Source dataset
uspto-grants-2014_10
Patent number
US08853213B2

Reaction notes

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