تفاعل #44307

معادلة التفاعل

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

المردود 13.0%

المذيبات

MeOH

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ice bath was removed
2. 2
   workup.WAITat 70° C. for three hours
3. 3
   درجة الحرارةThe reaction was cooled down to ambient temperature
4. 4
   أخرىquenched by 3 ml Sat'd Na2SO3
5. 5
   أخرىA precipitate was formed
6. 6
   ترشيحfiltered
7. 7
   استخلاصThe mother liquor was extracted with ethyl acetate (2×200 ml) twice
8. 8
   غسيلthe combined extracts were washed twice by Sat'd NaHCO3 (2×100 ml)
9. 9
   تجفيفdried over Na2SO4
10. 10
    تركيزconcentrated
11. 11
    أخرىto get the crude product which
12. 12
    أخرىa precipitate was formed
13. 13
    ترشيحThe solid was filtered

الإجراء التجريبي

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%).

المصدر