Reaktion #162723

Reaktionsgleichung

(Z)-ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate

(trimethylsilyl)isothiocyanate

→

title compound

Ausbeute 16.0%

6-(2,6-Dimethoxypyridin-3-yl)-1-(2-hydroxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Ausbeute 16.0%

Lösungsmittel

EtOAc

2-MeTHF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe cooled reaction mixture
2. 2
   Waschenwashed with a saturated aqueous sodium bicarbonate solution
3. 3
   SonstigeThe layers were separated
4. 4
   Einengenthe organic layer was concentrated in vacuo
5. 5
   SonstigeThe residue was triturated with MeOH
6. 6
   Filtrationthe resulting solids were collected by vacuum filtration

Vorschrift

To a solution of (Z)-ethyl 3-(2,6-dimethoxypyridin-3-yl)-3-((2-hydroxyethyl)amino)acrylate (100 mg, 0.34 mmol) in 2-MeTHF (1.0 mL) was added (trimethylsilyl)isothiocyanate (0.30 mL, 2.0 mmol) and the reaction mixture was heated at 80° C. for 4 hours. The cooled reaction mixture was diluted with EtOAc and washed with a saturated aqueous sodium bicarbonate solution. The layers were separated and the organic layer was concentrated in vacuo. The residue was triturated with MeOH and the resulting solids were collected by vacuum filtration to give the title compound (16 mg, 16%) as a white solid.

Quelle