Triethylamine → 4-(5-Chloropentylamino)-7-ethylamino-6-nitroquinazoline

Participants

Reaction Steps

Triethylamine (14.9 ml, 106.9 mmol) and 5-amino-1-pentanol (2.47 ml, 22.7 mmol) were added to a 1,4-dioxane solution (100 ml) of 4-chloro-7-ethylamino-6-nitroquinazoline (5.74 g, 22.7 mmol) obtained in Reference Example 13 under ice-cooling and the mixture was stirred at room temperature for 19 hours. The precipitated solid was filtered off, washed successively with water and ether and dried. To a solution of the resulting solid in 1,2-dichloroethane (40 ml), thionyl chloride (4.80 ml, 65.8 mmol) was added and the mixture was heated under reflux for 3 hours. After the solvent was distilled off, ice and a saturated aqueous solution of sodium bicarbonate were added and the mixture was extracted with chloroform. The organic layer was dried over a drying agent (magnesium sulfate), the drying agent was filtered off and the filtrate was concentrated under reduced pressure to give 7.15 g (93.3%) of the title compound as a crude product.

Provenance & Evidence