Reaktion #86419

Reaktionsgleichung

6-chloro-N-methylpyrimidin-4-amine

NaH

SEMCl

2,4-dichloro-3-isocyanato-1,5-dimethoxy-benzene

NH4Cl

→

title compound

Ausbeute 28.1%

1-(6-chloropyrimidin-4-yl)-3-(2,6-dichloro-3,5-dimethoxyphenyl)-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)urea

Ausbeute 28.1%

Lösungsmittel

DMF

DMF

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting mixture was stirred for 0.5 hour
2. 2
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 1 hour
3. 3
   Sonstigeto quench
4. 4
   Sonstigethe reaction
5. 5
   Extraktionextracted with EtOAc
6. 6
   WaschenThe combined extracts were washed with water and brine
7. 7
   Trocknendried over anhydrous Na2SO4
8. 8
   Filtrationfiltered
9. 9
   SonstigeThe filtrate was evaporated under vacuum
10. 10
    Sonstigeto give crude product, which
11. 11
    Sonstigewas purified by flash chromatography on silica

Vorschrift

To a solution of 6-chloro-N-methylpyrimidin-4-amine (Procedure 2A, step e; 460 g, 3.21 mmol) in DMF (15 mL) was added NaH (60%, 193 g, 4.81 mmol) at 0° C., and the mixture was stirred for 30 minutes at room temperature. A solution of 2,4-dichloro-3-isocyanato-1,5-dimethoxy-benzene (Procedure H, steps a-d; 1.03 g, 4.17 mmol) in DMF (5 mL) was added dropwise at room temperature. The resulting mixture was stirred for 0.5 hour. SEMCl (804 g, 4.81 mmol) in DMF (2 mL) was added. The reaction mixture was stirred at room temperature for 1 hour. Saturated aqueous NH4Cl was added to quench the reaction. The mixture was diluted with water and extracted with EtOAc. The combined extracts were washed with water and brine, dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum to give crude product, which was purified by flash chromatography on silica to obtain the title compound (470 mg, yield: 28%). MS (ESI): 521 [M+H]+.

Quelle