Reacción #63037

Ecuación de reacción

2-chloroacrylonitrile

1-amidino-4-phthalimidobutane hydrochloride

1,5-diazabicyclo[5,4,0]undec-5-ene

→

4-amino-2-(4-phthalimidobutyl)pyrimidine

Rendimiento 42.2%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled
2. 2
   Otroevaporated to dryness
3. 3
   workup.ADDITIONThe residue was treated with water (50 ml.)
4. 4
   Extracciónthe mixture extracted with ethyl acetate (2×50 ml.)
5. 5
   ExtracciónThe combined ethyl acetate extracts were extracted with N hydrochloric acid (3×30 ml.)
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   OtroThe ethyl acetate extracts were evaporated to dryness
8. 8
   Otrothe residue recrystallised from acetonitrile

Procedimiento

A solution of 2-chloroacrylonitrile (1.75 g.) in acetronitrile (10 ml.) was added over 15 minutes to an ice-cooled mixture of 1-amidino-4-phthalimidobutane hydrochloride (5.64 g.), acetonitrile (50 ml.) and 1,5-diazabicyclo[5,4,0]undec-5-ene (6.08 g.). The mixture was stirred for a further two hours and then evaporated to dryness. The residue was treated with water (50 ml.) and the mixture extracted with ethyl acetate (2×50 ml.). The combined ethyl acetate extracts were extracted with N hydrochloric acid (3×30 ml.) and the combined aqueous extracts neutralised with sodium bicarbonate and extracted with ethyl acetate. The ethyl acetate extracts were evaporated to dryness and the residue recrystallised from acetonitrile to give 4-amino-2-(4-phthalimidobutyl)pyrimidine (2.5 g.), m.p. 139°-140°.

Fuente