Phosphate → HCID 14999091, compound

Dry diisopropylamine (0.95 ml, 5.3 mmol) was added to dry tetrahydrofuran (3 ml). Further a butyllithium solution (3.6 ml, 5.8 mmol) in hexane was added dropwise at -40° C. The mixture was kept at -10° C. for 1 hour. Then a solution of 3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one (1 g, 4.8 mmol) in dry tetrahydrofuran (7 ml) was added dropwise at -20° to -10° C. After this reaction mixture had been kept between those temperatures for 1 hour, methyl iodide (0.75 g, 5.3 mmol) dissolved in dry tetrahydrofuran (2 ml) was added at -20° to -10° C. This reaction mixture was heated for 2 hours up to 0° C. and then kept at the same temperature for 2 hours. The resulting mixture, after addition of a phosphate buffer (pH 7.0), was extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure, and subjected to medium-pressure liquid chromatography (hexane-acetone) and then to recrystallization from a 1:1 ether-hexane mixture, giving 5,5,3-trimethyl-2-(3-pyridyl)thiazolidin-4-one (0.42 g, 39% yield). NMR (CDCl3) δ [ppm]; 1.62 (3 H, s), 1.68 (3 H, s), 2.74 (3 H, s), 5.51 (1 H, s). IR (nujol) [cm-1 ]; 1668, 1590, 1390, 1310, 1135, 1071, 1021.

1. waitAfter this reaction mixture had been kept between those temperatures for 1 hour
2. additionwas added at -20° to -10° C
3. temperatureThis reaction mixture was heated for 2 hours up to 0° C.
4. waitkept at the same temperature for 2 hours
5. extractionwas extracted with ethyl acetate
6. dry with materialThe extract was dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under reduced pressure
9. customto recrystallization from a 1:1 ether-hexane mixture

ORD record

ord-e622832b09d346a18c69a88f13fa6570

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05106860