Potassium Carbonate → HCID 25018649, compound

A mixture of 3-hydroxy-2-methyl-1H-pyridin-4-one (6.1 g, 48.7 mmol), potassium carbonate (17 g, 123 mmol), and CF3CH(OH)OCF3 (25 mL, 0.25 mol) was heated to reflux under a blanket of nitrogen for 30 h. The progress of the reaction was monitored by HPLC Method 1 (Example 24), which indicated 63% (peak percent area) of conversion to the product. The reaction mixture was diluted with methanol (50 mL), then filtered to remove solid particulates. The filtrate was evaporated to dryness to afford an oil. The oily residue was taken up in ethyl acetate (150 mL) and washed with a saturated ammonium chloride solution (80 mL). The organic fraction was collected and set aside. The pH of the aqueous fraction was adjusted to 6 with a dilute hydrochloric acid solution, and the resulting aqueous solution was extracted with ethyl acetate (2×40 mL). All the organic fractions were combined, then washed with saturated ammonium chloride, dried over Na2SO4, filtered and then evaporated to dryness to give an oil. On trituration with ether, 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one separated as a solid product and was collected by suction filtration (3.5 g, 33%). NMR data is described in Part C above.

1. temperaturewas heated
2. temperatureto reflux under a blanket of nitrogen for 30 h
3. filtrationfiltered
4. customto remove solid particulates
5. customThe filtrate was evaporated to dryness
6. customto afford an oil
7. washwashed with a saturated ammonium chloride solution (80 mL)
8. customThe organic fraction was collected
9. extractionthe resulting aqueous solution was extracted with ethyl acetate (2×40 mL)
10. washwashed with saturated ammonium chloride
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customevaporated to dryness
14. customto give an oil
15. customOn trituration with ether, 3-hydroxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one separated as a solid product
16. filtrationwas collected by suction filtration (3.5 g, 33%)

ORD record

ord-fa5bf6ff7de841329c2f426e6f13807b

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026261B2