Sodium Carbonate → 7-(4-Methanesulfonyl-phenyl)-4-methylsulfanylthieno[3,2-d]pyrimidine

Temperatur

100 °C

7-bromo-4-methylsulfanylthieno[3,2-d]pyrimidine (270 mg, 1.0 mmol) was added to 1,4-dioxane (10 mL), and 4-methanesulfonyl-phenylboronic acid (310 mg, 1.6 mmol), tetrakis(triphenylphosphine)palladium(0) (71 mg, 0.062 mmol), and 2N aqueous sodium carbonate (3.1 mL, 3.1 mmol) were sequentially added thereto. The air present in the reaction mixture was removed using a nitrogen balloon, and the reaction mixture was heated to 100° C. and stirred for 4 hours. The reaction was terminated by addition of sodium bicarbonate, and the reaction mixture was extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous magnesium sulfate 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 (260 mg) as a yellowish solid.

1. additionwere sequentially added
2. customThe air present in the reaction mixture was removed
3. customThe reaction was terminated by addition of sodium bicarbonate
4. extractionthe reaction mixture was extracted twice with ethyl acetate
5. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto obtain a foamy residue
8. customThe residue was crystallized in the presence of diethyl ether

ORD-Eintrag

ord-966ee56e458447039612c1857962c001

Quelldatensatz

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08853213B2