تفاعل #676758

معادلة التفاعل

4-(cyanomethylcarbamoyl)phenylboronic acid

5-bromo-2,4-diiodopyrimidine

potassium carbonate

→

4-(5-bromo-2-iodopyrimidin-4-yl)-N-(cyanomethyl)benzamide

المردود 50.2%

المذيبات

1,4-dioxane

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe cooled reaction mixture
2. 2
   استخلاصextracted twice with ethyl acetate
3. 3
   غسيلThe combined organic extracts were washed with water
4. 4
   تجفيفbrine, dried over anhydrous sodium sulfate
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىto give the crude product as a brown solid
8. 8
   أخرىThe crude material was purified by flash chromatography
9. 9
   غسيلeluting with 50% ethyl acetate/petroleum spirit

الإجراء التجريبي

To a mixture of 4-(cyanomethylcarbamoyl)phenylboronic acid (see example 3) (185 mg, 0.9 mmol) and 5-bromo-2,4-diiodopyrimidine (410 mg,1.0 mmol) in 1,4-dioxane (10 mL), was added 2M aqueous potassium carbonate (100 μL). The resulting mixture was stirred under nitrogen for 5 minutes then tetrakis(triphenylphophine)palladium(0) (52 mg, 0.045 mmol) was added under a nitrogen atmosphere. The mixture was heated at 80° C. overnight. The cooled reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic extracts were washed with water then brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product as a brown solid. The crude material was purified by flash chromatography, eluting with 50% ethyl acetate/petroleum spirit to give 4-(5-bromo-2-iodopyrimidin-4-yl)-N-(cyanomethyl)benzamide (200 mg, 35% over 2 steps). LC-ESI-MS (method B): rt 6.2 min.; m/z 443.0/445.0 [M+H]+.

المصدر