Reaktion #44307

Reaktionsgleichung

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

Ausbeute 13.0%

Lösungsmittel

MeOH

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice bath was removed
2. 2
   workup.WAITat 70° C. for three hours
3. 3
   TemperaturThe reaction was cooled down to ambient temperature
4. 4
   Sonstigequenched by 3 ml Sat'd Na2SO3
5. 5
   SonstigeA precipitate was formed
6. 6
   Filtrationfiltered
7. 7
   ExtraktionThe mother liquor was extracted with ethyl acetate (2×200 ml) twice
8. 8
   Waschenthe combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml)
9. 9
   Trocknendried over Na2SO4
10. 10
    Einengenconcentrated
11. 11
    Sonstigeto get the crude product which
12. 12
    Sonstigea precipitate was formed
13. 13
    FiltrationThe solid was filtered

Vorschrift

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%).

Quelle