反应 #1880991

反应方程式

Et3N

5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt

4-hydroxy-bicyclo[2.2.2]octane-1-carboxylic acid

HCl

H2O

NaOH

HATU

→

xanthine

收率 38.7%

8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-3,7-dihydro-purine-2,6-dione

收率 38.7%

溶剂

DMF

反应条件

后处理

1. 1
   其他The resulting reaction mixture
2. 2
   过滤The reaction mixture was filtered
3. 3
   其他to remove some of the precipitate
4. 4
   浓缩The filtrate was concentrated under reduced pressure
5. 5
   workup.STIRRINGThe reaction mixture was stirred
6. 6
   温度under reflux for 1 h
7. 7
   温度cooled to rt
8. 8
   过滤The resulting precipitate was collected by filtration
9. 9
   其他dried

实验过程

5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt (3.4 g) was dissolved in 80 mL of DMF along with 4-hydroxy-bicyclo[2.2.2]octane-1-carboxylic acid (2.5 g, 15 mmol). HATU (5.9 g, 1.05 eq) was added, followed by Et3N (8.30 mL, 4.05 eq). The resulting reaction mixture was stirred at rt overnight. The reaction mixture was filtered to remove some of the precipitate. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 60 mL of H2O containing 10 eq of NaOH (5.9 g). The reaction mixture was stirred under reflux for 1 h, cooled to rt and acidified to pH2 with concentrated HCl. The resulting precipitate was collected by filtration and dried to afford 1.85 g of the xanthine derivative.

来源