反应 #1821785

反应方程式

2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile

chloroformamidine hydrochloride

→

2,4-diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline

收率 46.9%

溶剂

diethyl ether

2-methoxyethyl ether

反应条件

后处理

1. 1
   其他This compound was prepared in a manner analogous to that of Step E of Example 1
2. 2
   其他Upon completion of the reaction
3. 3
   过滤The resultant solid was collected by filtration
4. 4
   workup.DISSOLUTIONwas dissolved in a hot mixture of 300 mL of water and 100 mL of n-propanol
5. 5
   过滤The solution was filtered hot through a sintered glass funnel
6. 6
   其他to remove some insoluble material
7. 7
   过滤The resultant solid was collected by filtration
8. 8
   其他dried at 60° C. under vacuum
9. 9
   workup.DISSOLUTIONThe solid was then dissolved in a solution of 10% methanol in methylene chloride
10. 10
    洗涤Elution
11. 11
    浓缩concentrated under reduced pressure

实验过程

This compound was prepared in a manner analogous to that of Step E of Example 1, using 2.7 grams (0.009 mole) of 2-amino-6-methyl-5-[(4-trifluoromethylphenyl)ethynyl]benzonitrile and 1.2 grams (0.011 mole) of chloroformamidine hydrochloride in 10 mL of 2-methoxyethyl ether. Upon completion of the reaction, the reaction mixture was diluted with 200 mL of diethyl ether. The resultant solid was collected by filtration, and was dissolved in a hot mixture of 300 mL of water and 100 mL of n-propanol. The solution was filtered hot through a sintered glass funnel to remove some insoluble material. The filtrate was then made basic with 100 mL of concentrated ammonium hydroxide. The resultant solid was collected by filtration, and dried at 60° C. under vacuum. The solid was then dissolved in a solution of 10% methanol in methylene chloride, and the solution was subjected to column chromatography on silica gel. Elution was accomplished using 10% methanol in methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 1.6 grams of 2,4-diamino-5-methyl-6-[1-chloro-2-(4-trifluoromethylphenyl)ethenyl]quinazoline, mp >300° C. The NMR spectrum was consistent with the proposed structure.

来源