تفاعل #2199590

معادلة التفاعل

product

4-Amino-7-(2′-methyl-2′,3′,5′-tris-O-acetyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

nitric acid

sulfuric acid

→

4-Amino-7-(2′-methyl-2′,3′,5′-tris-O-acetyl-β-D-ribofuranosyl)-5-nitro-7H-pyrrolo[2,3-d]pyrimidine

المذيبات

dichloromethane

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   أخرىThe reaction was quenched with ice cold saturated sodium bicarbonate solution
3. 3
   أخرىThe quenched reaction
4. 4
   استخلاصextracted with dichloromethane
5. 5
   تجفيفThe organic layer was dried over sodium sulfate
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىThe residue was purified
8. 8
   أخرىto give 600 mg (36%)

الإجراء التجريبي

A solution of the product from Step 4 (1.5 g, 3.69 mmol) in dichloromethane (25 mL) was cooled to 0° C. and a 1:1 mixture of fuming nitric acid and sulfuric acid (4 mL) was added dropwise and the reaction was vigorously stirred at 0° C. for 20 min. The reaction was quenched with ice cold saturated sodium bicarbonate solution. The quenched reaction was diluted with water and extracted with dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by plating on silica gel with dichloromethane and eluded by ramping to 5% methanol in dichloromethane to give 600 mg (36%);

المصدر