Thiazolidinedione → HCID 58313031, compound

Temperature

90 °C

A 30 mL round-bottomed vial was charged with 4-methyl-2-(methylthio)-6-(trifluoromethyl)pyrimidine (0.500 g, 2.4 mmol, 1 equiv.), ethanol (5 mL, 0.48 M), selenium dioxide (0.293 mg, 2.6 mmol, 1.1 equiv.), and the reaction mixture was shaken at 90° C. for 40 h and then RT for 14 d. The crude reaction mixture was then treated with thiazolidine-2,4-dione (0.281 g, 2.4 mmol, 1 equiv.), triethylamine (1.0 mL, 7.20 mmol, 3 equiv.) and the reaction mixture was shaken for 16 h at 80° C. The solvent was concentrated under reduced pressure and the residue was partitioned between EtOAc (30 mL) and saturated NaHCO3 (25 mL). The aqueous layer was extracted with EtOAc (2×10 mL) and the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified using the Biotage (SiO2, 10 g cartridge, CH2Cl2/MeOH 99:1 to 9:1) that afforded 270 mg of partially purified product that was re-purified using the Biotage (SiO2, 10 g cartridge, Hexanes/EtOAc 90:10 to 0:1 then CH2Cl2/MeOH 99:1 to 9:1) afforded 212 mg of yellow solid that was still not completely pure but was used directly in the next step without further purification.

1. waitRT for 14 d
2. customThe crude reaction mixture
3. stirringthe reaction mixture was shaken for 16 h at 80° C
4. concentrationThe solvent was concentrated under reduced pressure
5. customthe residue was partitioned between EtOAc (30 mL) and saturated NaHCO3 (25 mL)
6. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
7. dry with materialthe combined organic layer was dried over Na2SO4
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified
10. customthat afforded 270 mg of partially purified product that
11. customwas re-purified

ORD record

ord-c190325d8b334bc09e972cd73241c48c

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09157077B2