Reacción #44307

Ecuación de reacción

5-bromo-N*3*-quinazolin-6-ylmethyl-pyrazine-2,3-diamine

isoamyl nitrite

→

6-(6-Bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinazoline

Rendimiento 13.0%

Disolventes

MeOH

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe ice bath was removed
2. 2
   workup.WAITat 70° C. for three hours
3. 3
   TemperaturaThe reaction was cooled down to ambient temperature
4. 4
   Otroquenched by 3 ml Sat'd Na2SO3
5. 5
   OtroA precipitate was formed
6. 6
   Filtraciónfiltered
7. 7
   ExtracciónThe mother liquor was extracted with ethyl acetate (2×200 ml) twice
8. 8
   Lavadothe combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml)
9. 9
   Secadodried over Na2SO4
10. 10
    Concentraciónconcentrated
11. 11
    Otroto get the crude product which
12. 12
    Otroa precipitate was formed
13. 13
    FiltraciónThe solid was filtered

Procedimiento

To the solution of 5-bromo-N*3*-quinazolin-6-ylmethyl-pyrazine-2,3-diamine (1.02 g) in anhydrous DMF (12 mL) was added isoamyl nitrite (0.5 mL, 1.2 eq) at 0° C. dropwise. The ice bath was removed and the mixture was stirred for 5 minutes at room temperature, then at 70° C. for three hours. The reaction was cooled down to ambient temperature and quenched by 3 ml Sat'd Na2SO3. A precipitate was formed, and filtered. The mother liquor was extracted with ethyl acetate (2×200 ml) twice, and the combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml), dried over Na2SO4, and concentrated to get the crude product which was dissolved in MeOH (10 ml), and a precipitate was formed. The solid was filtered to get 6-(6-Bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-quinazoline (0.112 g, yield 13%).

Fuente