반응 #705102

반응 방정식

2-amino-6-phenyl-pyrido-[2,3-d]pyrimidin-7-ol

dichloromethane

thionyl chloride

→

title compound

수율 44.4%

N7 -Butyl-6-phenyl-pyrido[2,3-d]pyrimidine-2,7-diamine

수율 44.4%

용매

dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONaddition
3. 3
   온도the suspension was heated
4. 4
   온도to reflux
5. 5
   기타The solvents were removed in vacuo
6. 6
   온도maintaining the temperature below 60° C
7. 7
   workup.ADDITIONThe resulting solid was added
8. 8
   온도with cooling to 250 mL of n-butylamine
9. 9
   온도the suspension refluxed for 6 hours
10. 10
    workup.STIRRINGwith stirring
11. 11
    여과filtered
12. 12
    기타the volatile components of the filtrate removed on a rotary evaporator in vacuo
13. 13
    기타The viscous oil was partitioned between diethyl ether and water
14. 14
    기타the layers were separated
15. 15
    세척the ethereal layer was washed with water
16. 16
    건조The organic layer was dried over anhydrous magnesium sulfate
17. 17
    여과filtered
18. 18
    기타evaporated
19. 19
    기타The residue was partitioned between diethyl ether
20. 20
    workup.ADDITIONdilute 1N HCl
21. 21
    세척The aqueous layer was washed three times with diethylether
22. 22
    workup.ADDITIONby addition of sodium hydroxide
23. 23
    여과The solid product was collected by filtration
24. 24
    기타dried in vacuo

실험 절차

To a mixture of 23.8 g of 2-amino-6-phenyl-pyrido-[2,3-d]pyrimidin-7-ol prepared above in Example 8, 250 mL of dichloromethane, and 77.5 mL of dimethylformamide was added dropwise with cooling 36 mL of thionyl chloride keeping the temperature below 15° C. Following complete addition, the suspension was heated to reflux with stirring for 5 hours. The solvents were removed in vacuo maintaining the temperature below 60° C. The resulting solid was added with cooling to 250 mL of n-butylamine and the suspension refluxed for 6 hours with stirring. The reaction mixture was allowed to cool to room temperature, filtered, and the volatile components of the filtrate removed on a rotary evaporator in vacuo. The viscous oil was partitioned between diethyl ether and water, the layers were separated, and the ethereal layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and evaporated. The residue was partitioned between diethyl ether and dilute 1N HCl. The aqueous layer was washed three times with diethylether and made alkaline to pH 12 by addition of sodium hydroxide. The solid product was collected by filtration and dried in vacuo to afford 6.5 g of the title compound N7 -butyl-6-phenyl-pyrido[2,3-d]pyrimidine-2,7-diamine, mp 174-181° C. dec.

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