反応 #3507

反応方程式

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

dichloromethane

thionyl chloride

→

title compound

収率 44.4%

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

収率 44.4%

溶媒

dimethylformamide

反応条件

後処理

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

実験手順

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.

出典