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1-3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1902 mg, 1 mmol) was added to a solution of 6-amino-4[(3-chlorophenyl)amino]quinazoline (136 mg, 0.5 mmol) acrylic acid (74 mg, 1.0 mmol) and pyridine (201 mg, 2.5 mmol) in THF/DMF (4:1, 2.5 mL), stirred under nitrogen at 0° C. After 20 minutes the reaction mixture was stirred at 25° C. for 3 hours, and then poured onto water (12.5 mL), and extracted with EtOAc (2×10 mL). The combined extracts were treated with dilute hydrochloric acid (0.5 M, 10 mL), and the precipitate was collected by Buchner filtration, rinsed with water (10 mL), ether (2×10 mL), and air dried to give N-[4-[(3-chlorophenyl)amino]quinazolin-6-yl]acrylamide hydrochloride (93 mg, 48%) as a dull yellow solid, mp 223-227° C.

1. stirringAfter 20 minutes the reaction mixture was stirred at 25° C. for 3 hours
2. additionpoured onto water (12.5 mL)
3. extractionextracted with EtOAc (2×10 mL)
4. additionThe combined extracts were treated with dilute hydrochloric acid (0.5 M, 10 mL)
5. filtrationthe precipitate was collected by Buchner filtration
6. washrinsed with water (10 mL), ether (2×10 mL), and air
7. customdried