Réaction #44307

Équation de réaction

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

Rendement 13.0%

Solvants

MeOH

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe ice bath was removed
2. 2
   workup.WAITat 70° C. for three hours
3. 3
   TempératureThe reaction was cooled down to ambient temperature
4. 4
   Autrequenched by 3 ml Sat'd Na2SO3
5. 5
   AutreA precipitate was formed
6. 6
   Filtrationfiltered
7. 7
   ExtractionThe mother liquor was extracted with ethyl acetate (2×200 ml) twice
8. 8
   Lavagethe combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml)
9. 9
   Séchagedried over Na2SO4
10. 10
    Concentrationconcentrated
11. 11
    Autreto get the crude product which
12. 12
    Autrea precipitate was formed
13. 13
    FiltrationThe solid was filtered

Mode opératoire

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%).

Source