تفاعل #2199587

معادلة التفاعل

NaOMe

compound

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

glycine methylester mono hydrochloride

→

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

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONthis mixture was added to the methanolic solution
2. 2
   تركيزConcentrated
3. 3
   أخرىreaction in vacuo
4. 4
   أخرىpurified on flash silica gel chromatography with a 0-5.0% MeOH gradient in DCM
5. 5
   أخرىto afford 100 mg (60%)

الإجراء التجريبي

The compound from Step 3 (150 mg, 0.319 mmol) was dissolved in anhydrous MeOH (3 mL). Meanwhile glycine methylester mono hydrochloride (48 mg, 0.383 mmol) was neutralized with a 0.5M solution NaOMe (766 μl, 0.383 mmol) and this mixture was added to the methanolic solution containing nucleoside and the mixture was heated to 75° C. for 1.5 hours. Concentrated reaction in vacuo and purified on flash silica gel chromatography with a 0-5.0% MeOH gradient in DCM to afford 100 mg (60%).

المصدر