Phosphate → HCID 14999090, compound

Dry diisopropylamine (1 ml, 5.7 mmol) was added to dry tetrahydrofuran (3 ml), and a butyllithiium solution (3.9 ml, 6.2 mmol) in hexane was added dropwise at -40° C., the mixture was kept at -10° C. for 1 hour. A solution of 3-methyl-2-(3-pyridyl)thiazolidin-4-one (1 g, 5.2 mmol) in dry tetrahydrofuran (7 ml) was added dropwise to the mixture at -20° to -10° C. After this reaction mixture had been kept between those temperatures for 1 hour, there were added at -10° C. 1-bromobutane (0.78 g, 5.7 mmol) dissolved in tetrahydrofuran (2 ml), sodium iodide (0.77 g, 5.2 mmol), and hexamethylphosphorotriamide (1 ml). This reaction mixture was kept at room 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 by evaporation under reduced pressure. The residue was chromatographed on silica gel (hexeneethyl acetate), giving 5-butyl-3-methyl-2-(3-pyridyl)-thiazolidin-4-one (250 mg, 20% yield). NMR (CDCl3) δ [ppm]; 0.93 (3 H, t, J=7.0 Hz), 1.2-2.3 (6 H, m), 2.74 (3 H, m), 3.9-4.3 (1 H, m), 5.4-5.5 (1 H, m). IR (CHCl3) [cm-1 ]; 2925, 2855, 1670, 1590, 1578, 1390, 1303, 1020.

1. waitAfter this reaction mixture had been kept between those temperatures for 1 hour
2. additionthere were added at -10° C
3. waitThis reaction mixture was kept at room temperature for 2 hours
4. extractionwas extracted with ethyl acetate
5. dry with materialThe extract was dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationThe filtrate was concentrated by evaporation under reduced pressure
8. customThe residue was chromatographed on silica gel (hexeneethyl acetate)

ORD record

ord-895f4944e81c440685fde8332496aaa7

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05106860