反应详情

1.26 g (3.45 mmoles) of 2-amino-5-(4-chlorophenoxy)-4-(4-hydroxyanilino)pyrimidine hydrochloride (see Example 11) and 0.05 g of 4-dimethylaminopyridine were dissolved in 3.2 g of dry N,N-dimethylformamide. 5.3 g of acetic anhydride was added, and the container was sealed. After 5 days at 24° C., 100 mL of CH2Cl2 were added to the reaction mixture and stirred with 150 mL of cold saturated aqueous NaHCO3. The organic layer was then washed twice with 250 mL of water, then with 200 mL of brine and dried over Na2SO4. After filtering off the salt, the filtrate was applied to a Silica Gel 60 column (2.5×7.5 cm) which had been preequalibrated with hexanes. The column was eluted with 200 mL hexanes, a mixture of 100 mL hexanes and 200 mL CH2Cl2, and 500 mL CH2Cl2. Fractions with product which was pure by TLC (EtOAc; Rf 0.6) were pooled and spin evaporated to a waxy solid. This solid was removed from the flask with the aid of hot hexanes. After cooling, solids were collected by filtration and washed with hexanes. After drying in vacuo at 89° C. for 16 hours, the product, a cream colored powder, 0.14 g (11% yield), was obtained, mp 132-133° C.

1. customthe container was sealed
2. washThe organic layer was then washed twice with 250 mL of water
3. dry with materialwith 200 mL of brine and dried over Na2SO4
4. filtrationAfter filtering off the salt
5. washThe column was eluted with 200 mL hexanes
6. additiona mixture of 100 mL hexanes and 200 mL CH2Cl2, and 500 mL CH2Cl2
7. customspin evaporated to a waxy solid
8. customThis solid was removed from the flask with the aid of hot hexanes
9. temperatureAfter cooling
10. filtrationsolids were collected by filtration
11. washwashed with hexanes
12. customAfter drying in vacuo at 89° C. for 16 hours
13. customwas obtained