반응 #481906

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7-amino-4-(3-bromoanilino)-quinazoline

monoethyl fumarate

1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide HCl

7-Amino-4-(3-bromoanilino)-quinazoline

→

desired product

수율 23.5%

3-[4-(3-Bromo-phenylamino)-quinazolin-7-ylcarbamoyl]-acrylic acid ethyl ester

수율 23.5%

용매

dimethylformamide

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후처리

1. 1
   기타the ice bath was removed
2. 2
   온도to warm to room temperature where it
3. 3
   workup.STIRRINGstirred for 15 hours
4. 4
   workup.ADDITIONThe reaction was poured into cold water
5. 5
   workup.ADDITIONthe suspension was made basic with the addition of a saturated sodium bicarbonate solution
6. 6
   여과The resulting solid was collected by filtration
7. 7
   세척washed with water
8. 8
   기타recrystallized from 50 mL of ethanol

실험 절차

To an ice cold solution of 0.158 g of 7-amino-4-(3-bromoanilino)-quinazoline and 0.216 g of monoethyl fumarate in 3 mL of dry dimethylformamide was added 0.288 g of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide HCl (EDAC). 7-Amino-4-(3-bromoanilino)-quinazoline can be made by methods well-known to those skilled in the art. See, for example, J Med Chem, 1995:3482, which is hereby incorporated by reference. After stirring at 50° C. for 5 minutes, the ice bath was removed, and the reaction was permitted to warm to room temperature where it stirred for 15 hours. The reaction was poured into cold water, and the suspension was made basic with the addition of a saturated sodium bicarbonate solution. The resulting solid was collected by filtration, washed with water, and then recrystallized from 50 mL of ethanol to afford 0.052 g of the desired product, mp >260° C.

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