反応 #1528412

反応方程式

20

1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazole-4-carboxamide

HBTU

HOBt

N-methylmorpholine

→

compound 21

(1-{9-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-aminopurin-2-yl}pyrazol-4-yl)-N-(cyclopentyl)carboxamide

溶媒

dichloromethane

反応条件

後処理

1. 1
   洗浄The mixture was then washed with 10% citric acid, saturated NaHCO3, brine
2. 2
   乾燥dried over MgSO4
3. 3
   その他The solvent was removed
4. 4
   workup.ADDITIONthe residue was treated with 5 mL 0.5N NH4F/MeOH
5. 5
   温度The solution was heated
6. 6
   温度at reflux for 24 h
7. 7
   その他The solvent was evaporated
8. 8
   その他the residue was purified by preparative TLC

実験手順

The trisilyl derivative acid 20 (0.14 g, 0.2 mmol) was then dissolved in 5 mL dichloromethane. To the solution was added HBTU (0.19 g, 0.4 mmol), HOBt (0.076 g, 4 mmol), N-methylmorpholine (0.04 g, 0.4 mmol) and cat. DMAP. The mixture was allowed to stir at RT for 24 h. The mixture was then washed with 10% citric acid, saturated NaHCO3, brine and dried over MgSO4. The solvent was removed and the residue was treated with 5 mL 0.5N NH4F/MeOH. The solution was heated at reflux for 24 h. The solvent was evaporated and the residue was purified by preparative TLC to afford compound 21, MS 445.26 (M+1).

出典