Hydrochloric Acid → HCID 67282310, Verbindung

Temperatur

40 °C

In each of three parallel synthesis tubes equipped with a magnetic stir bar was placed 5-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (0.50 g, 2.24 mmol), a 36.5% by wt formaldehyde solution (6 mL, 80.4 mmol), and a 6.00 N sodium hydroxide solution (0.45 mL, 2.7 mmol). The resulting solution was heated to about 40° C. for overnight. Analysis by HPLC Method 1 (Example 24) indicated consumption of the starting material. The contents of the three tubes were combined, and the resulting solution was cooled in an ice-water bath. A 6.00 N hydrochloric acid solution (1.1 mL, 6.6 mmol) was added to adjust the pH of the solution to about 6. The mixture was concentrated in vacuo to remove most of the solvent to give a solid/liquid mixture. To the mixture was added methanol (100 mL), and the mixture was stirred for 1 h. The first crop of the solid was collected by suction filtration and washed with de-ionized water thoroughly to give 3-hydroxy-2-hydroxymethyl-1-methyl-6-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one (0.83 g, 48% yield, HPLC Method 1 (Example 24), RT=7.7 min, HPLC purity (peak percent area): 99.2% at λ=280 nm). 1H NMR (DMSO-d6+D2O) δ ppm: 6.53 (s, 1H), 5.54 (q, J=6.5 Hz, 1H), 4.67 (s, 2H), 3.76 (s, 3H); MS-ESI (m/z) 254.1 [M+1]+, 236.1, 208.1 (100%), 139.2.

1. customIn each of three parallel synthesis tubes
2. customequipped with a magnetic stir bar
3. customconsumption of the starting material
4. temperaturethe resulting solution was cooled in an ice-water bath
5. concentrationThe mixture was concentrated in vacuo
6. customto remove most of the solvent
7. customto give a solid/liquid mixture
8. filtrationThe first crop of the solid was collected by suction filtration
9. washwashed with de-ionized water thoroughly

ORD-Eintrag

ord-6459cf46ece241ef8fe39d0ebbecf9f4

Quelldatensatz

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08026261B2