反应详情

To 0.7 g of sodium hydride (14.5 mmol) stirred in 40 ml of dry dimethylformamide under nitrogen was added dropwise over a 15 minute period a solution of 2.0 g of 3-(hydroxymethyl)-4H-pyrimido[2,1-a]isoquinolin-4-one (8.3 mmol) in 40 ml of warm dimethylformamide. After stirring for 1 hour, 1.58 g of diethylaminoethyl chloride (11.6 mmol) was added dropwise over a 15 minute period. The reaction mixture was stirred for 3 hours, then poured onto ice-water and extracted 3 times with 500 ml of methylene chloride. The extracts were dried and concentrated in vacuo to yield a semi-solid, to which 15 ml of isopropanolic hydrochloric acid solution and diethyl ether were added. The crystalline solid which formed was collected and washed with ether to yield 3-[[2-(diethylamino)ethoxy]methyl]-4H-pyrimido[2,1-a]isoquinolin-4-one dihydrochloride (0.973 g; 28% yield) of the formula: ##STR24## having a melting point of 128.7° C. and the following elemental analysis:

1. stirringThe reaction mixture was stirred for 3 hours
2. additionpoured onto ice-water
3. extractionextracted 3 times with 500 ml of methylene chloride
4. customThe extracts were dried
5. concentrationconcentrated in vacuo
6. customto yield a semi-solid
7. customThe crystalline solid which formed
8. customwas collected
9. washwashed with ether