Phosphorus oxychloride → 4-Chloro-2-(methylthio)thieno[2,3-d]pyrimidine

Temperatur

0 °C

2-Methylsulfanyl-3H-thieno[2,3-d]pyrimidin-4-one (12 g, 60.5 mmol) was combined with POCl3 (56 mL), and the resulting mixture was heated to reflux for about 1 hour. The reaction mixture was concentrated under reduced pressure at 50° C. The residue was diluted with ethyl acetate (700 mL) at 0° C. Saturated sodium bicarbonate solution (600 mL) was added slowly. The resulting mixture was stirred vigorously at 0° C. for one hour and the layers were separated. Saturated sodium bicarbonate solution (600 mL) was added to the organic layer at 0° C., and the mixture was stirred vigorously for 20 minutes. The layers were separated. Brine (600 mL) was added to the organic layer and stirred vigorously for 5 minutes, and the layers were again separated. The organic layer was dried over magnesium sulfate, filtered and concentrated to afford the title compound (10.7 g) as a dark tan powder (M+=216, M.P.=105.0-107.4° C.).

1. temperaturethe resulting mixture was heated
2. temperatureto reflux for about 1 hour
3. concentrationThe reaction mixture was concentrated under reduced pressure at 50° C
4. additionThe residue was diluted with ethyl acetate (700 mL) at 0° C
5. additionSaturated sodium bicarbonate solution (600 mL) was added slowly
6. customthe layers were separated
7. additionSaturated sodium bicarbonate solution (600 mL) was added to the organic layer at 0° C.
8. stirringthe mixture was stirred vigorously for 20 minutes
9. customThe layers were separated
10. additionBrine (600 mL) was added to the organic layer
11. stirringstirred vigorously for 5 minutes
12. customthe layers were again separated
13. dry with materialThe organic layer was dried over magnesium sulfate
14. filtrationfiltered
15. concentrationconcentrated

ORD-Eintrag

ord-1934601953e5447c8a5dbb3d41b9e7fb

Quelldatensatz

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07439247B2