تفاعل #165804

معادلة التفاعل

ether

DIPEA

4-[5-amino-6-[[(6-aminopyridine-2-carbonyl)amino]carbamoyl]pyrazin-2-yl]-N,N-dimethyl-benzamide

dibromo(triphenyl)phosphorane

→

product

المردود 54.0%

4-[5-amino-6-[5-(6-amino-2-pyridyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide

المردود 54.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled in an ice bath
2. 2
   أخرىThe precipitate was isolated by filtration
3. 3
   غسيلwashed with small amount of acetonitrile giving a pale yellow solid
4. 4
   أخرىThe solid was triturated in hot acetonitrile
5. 5
   درجة الحرارةcooled
6. 6
   ترشيحfiltered
7. 7
   غسيلwashed acetonitrile

الإجراء التجريبي

To a suspension of 4-[5-amino-6-[[(6-aminopyridine-2-carbonyl)amino]carbamoyl]pyrazin-2-yl]-N,N-dimethyl-benzamide (80 mg, 0.1903 mmol) in anhydrous acetonitrile (1.600 mL) cooled in an ice bath, was added DIPEA (73.78 mg, 99.43 μL, 0.5709 mmol) followed by dibromo(triphenyl)phosphorane (104.4 mg, 0.2474 mmol) portionwise. The resulting mixture was stirred at room temperature for 30 min. The precipitate was isolated by filtration, washed with small amount of acetonitrile giving a pale yellow solid. The solid was triturated in hot acetonitrile, cooled, filtered and washed acetonitrile then ether to give the pure product (36.1 mg, 54% yield); 1H NMR (400 MHz, DMSO) d 2.98-3.02 (m, 6H), 6.53 (br s, 2H), 6.69 (m, 1.5H), 7.16 (m, 0.51H), 7.16 (m, 1H), 7.53-7.66 (m, 3H), 8.11 (m, 2H) and 8.94 (s, 1H) ppm; MS (ES+) 403.29

المصدر