Reacción #66624

Ecuación de reacción

2-(6-isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile

guanidine carbonate

sodium methoxide

HCl

→

5-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine

Disolventes

ethanol

Diethyl ether

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroformed
2. 2
   OtroThe solid that had formed
3. 3
   Filtraciónwas collected by filtration
4. 4
   Lavadowashed with diethyl ether
5. 5
   Otrodried under vacuum at 45 C
6. 6
   Otroto give 171 mg

Procedimiento

5-(6-Isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-pyrimidine-2,4-diamine was prepared from 2-(6-isopropyl-1,3-dimethyl-1H-indol-5-yloxy)-4-methoxy-but-2-enenitrile by treatment with guanidine carbonate and sodium methoxide using the procedure of step 7 of Example 2 above. This material was dissolved in 2.5 ml absolute ethanol, and 820 ml of 1 N HCl in diethyl ether was added with stirring. Diethyl ether was added slowly until small crystals formed, and the solution was then placed in a −10 C freezer for 18 hours. The solid that had formed was collected by filtration, washed with diethyl ether, and dried under vacuum at 45 C. to give 171 mg. of the hydrochloride salt, Mp: 185.1° C.

Fuente