2-Methylpyridine → HCID 59834315, compound

Temperature

80 °C

To a cooled (ice bath) mixture of (2-chlorophenyl)-(4-hydroxy-2-methylsulfanylpyrimidin-5-yl)methanone (18.72 g, 66 mmol) and picoline (3.95 mL, 39.6 mmol) was added dropwise phosphoryl chloride (37.3 mL, 396 mmol) via an addition funnel. The resulting mixture was removed from the ice bath and heated to 80° C. for 2 hours. The reaction was cooled to ambient temperature and poured onto ice (250 mL). Ethyl acetate was added and the layers were partitioned and separated. The organic layer was further washed with two consecutive solutions of saturated sodium bicarbonate (150 mL) followed by brine (150 mL). The aqueous layers were back extracted with ethyl acetate (2×150 mL). The combined ethyl acetate layers were dried over magnesium sulfate, filtered and concentrated to give the product as a yellow solid (17.36 g, (M+H)+=299.

1. temperatureTo a cooled
2. customThe resulting mixture was removed from the ice bath
3. temperatureThe reaction was cooled to ambient temperature
4. additionpoured onto ice (250 mL)
5. additionEthyl acetate was added
6. customthe layers were partitioned
7. customseparated
8. washThe organic layer was further washed with two consecutive solutions of saturated sodium bicarbonate (150 mL)
9. extractionThe aqueous layers were back extracted with ethyl acetate (2×150 mL)
10. dry with materialThe combined ethyl acetate layers were dried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-82249a4211df4472a2bfc19c5b53edc3

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566708B2