反応 #44307

反応方程式

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

収率 13.0%

溶媒

MeOH

DMF

反応条件

後処理

1. 1
   その他The ice bath was removed
2. 2
   workup.WAITat 70° C. for three hours
3. 3
   温度The reaction was cooled down to ambient temperature
4. 4
   その他quenched by 3 ml Sat'd Na2SO3
5. 5
   その他A precipitate was formed
6. 6
   ろ過filtered
7. 7
   抽出The mother liquor was extracted with ethyl acetate (2×200 ml) twice
8. 8
   洗浄the combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml)
9. 9
   乾燥dried over Na2SO4
10. 10
    濃縮concentrated
11. 11
    その他to get the crude product which
12. 12
    その他a precipitate was formed
13. 13
    ろ過The solid was filtered

実験手順

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%).

出典