Reacción #979034

Ecuación de reacción

NaOH

sodium acetate trihydrate

1,1-dibromo-3-fluoro-3-methylbutan-2-one

aminoguanidine bicarbonate

→

title compound

Rendimiento 51.0%

3-Amino-5-(1-fluoro-1-methylethyl)-1,2,4-triazine

Rendimiento 51.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux under nitrogen for 40 min
2. 2
   workup.STIRRINGthe mixture was stirred under nitrogen for a further 3 days
3. 3
   FiltraciónThe mixture was filtered
4. 4
   Lavadothe solid was washed with water twice
5. 5
   Otrodried under vacuum at 60° C.

Procedimiento

A stirred solution of sodium acetate trihydrate (23.07 g, 80.7 mmol) and 1,1-dibromo-3-fluoro-3-methylbutan-2-one (21.14 g, 80.7 mmol) in water (80 ml) was heated at reflux under nitrogen for 40 min, then allowed to cool to room temperature before adding solid aminoguanidine bicarbonate (10.99 g, 80.7 mmol). The mixture was stirred at room temperature for 5 h, then 4 N aqueous NaOH solution (40.4 ml, 162 mmol) was added and the mixture was stirred under nitrogen for a further 3 days. The mixture was filtered and the solid was washed with water twice, then dried under vacuum at 60° C. to give 6.40 g (51%) of the title compound as a yellow-brown solid: 1H NMR (360 MHz, DMSO-d6) δ 1.63 (6H, d, J 22.2), 7.32 (2H, br s), 8.73 (1H, d, J 1.0); MS (ES+) m/z 157 [M+H]+.

Fuente