反应详情

Methanol (5 mL) was added to 2-Amino-4-(5-formyl-2-methyl-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (100 mg, 0.29 mmol) and propylamine (0.586 mmol) then added to resulting suspension. Reaction mixture was heated to reflux (affording homogeneous brown solution) for 4 hours then allowed to cool to ambient temperature. Sodium borohydride (23 mg; 0.58 mmol) was added and reaction mixture stirred for 30 mins. Methanol was removed in vacuo and the residue was partitioned between water (20 mL) and ethyl acetate (20 mL). The phases were separated and organic phase was dried over Na2SO4 and filtered, and filtrate solvents removed in vacuo to afford brown solid which was suspended 2.0M ethylamine in methanol solution (5.0 mL, 10 mmol) and heated in sealed tube at 85 degrees C. overnight. Reaction mixture was allowed to cool and solvents removed in vacuo to afford a brown solid which was triturated in hot ethyl acetate, filtered and dried to afford title product as light-brown solid (50 mg, 45%)

1. additionthen added
2. customto resulting suspension
3. customReaction mixture
4. temperaturewas heated
5. temperatureto reflux
6. custom(affording homogeneous brown solution) for 4 hours
7. customreaction mixture
8. customMethanol was removed in vacuo
9. customthe residue was partitioned between water (20 mL) and ethyl acetate (20 mL)
10. customThe phases were separated
11. dry with materialorganic phase was dried over Na2SO4
12. filtrationfiltered
13. customfiltrate solvents removed in vacuo
14. customto afford brown solid which
15. temperatureheated in sealed tube at 85 degrees C
16. customovernight
17. customReaction mixture
18. temperatureto cool
19. customsolvents removed in vacuo
20. customto afford a brown solid which
21. customwas triturated in hot ethyl acetate
22. filtrationfiltered
23. customdried