Hydrochloric Acid → 3-(Methylthio)-6-phenyl-5-(pyridin-3-yl)-1,2,4-triazine

To a suspension of 2-(hydroxyimino)-1-phenyl-2-(pyridin-3-yl)ethanone (0.434 g, 1.918 mmol) in a 1:1 mixture of EtOH/H2O (8.0 mL) was added hydrazinecarbothioamide (0.262 g, 2.88 mmol) followed by concentrated HCl (0.307 mL, 3.84 mmol). The reaction was stirred at room temperature for 1 h then heated to 90° C. overnight. Upon completion, the reaction mixture was neutralized with saturated NaHCO3. The solid formed was filtered and rinsed with H2O. The solid was added to a solution of potassium carbonate (1.326 g, 9.59 mmol) in H2O (50 mL) and heated to 90° C. overnight. Upon completion, the reaction mixture was cooled to room temperature then placed in an ice bath. To the ice cooled mixture was added iodomethane (0.119 mL, 1.918 mmol). The reaction was stirred at 0° C. and slowly warmed to room temperature. After stirring overnight, the solution was extracted with CH2Cl2 (3×75 mL), washed with H2O, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow solid (0.152 g). LCMS m/z=281.1 [M+H]+.

1. temperaturethen heated to 90° C. overnight
2. customThe solid formed
3. filtrationwas filtered
4. washrinsed with H2O
5. temperatureheated to 90° C. overnight
6. temperatureUpon completion, the reaction mixture was cooled to room temperature
7. customthen placed in an ice bath
8. stirringThe reaction was stirred at 0° C.
9. temperatureslowly warmed to room temperature
10. stirringAfter stirring overnight
11. extractionthe solution was extracted with CH2Cl2 (3×75 mL)
12. washwashed with H2O, brine
13. dry with materialdried over MgSO4
14. concentrationconcentrated
15. customThe residue was purified by silica gel column chromatography

ORD record

ord-ca0b168225e74b84afed347f92add05c

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940891B2