Reacción #1855

Ecuación de reacción

sodium hydride

IV

(E)-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

iodomethane

diisopropylamine

→

compound V

Rendimiento 76.1%

(E)-N-Methyl-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

Rendimiento 76.1%

Disolventes

water

1,2-dimethyoxyethane

DMF

water

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   Temperaturacooled
3. 3
   Extracciónextracted with chloroform (7×50 mL)
4. 4
   Otrodried (Na2 SO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated by rotary evaporation
7. 7
   OtroThe residue was dried under high vacuum at ambient temperature
8. 8
   Otroto give a red-brown oil
9. 9
   OtroThe oil was chromatographed on silica gel (50 g)
10. 10
    Lavadoeluting with ethyl acetate
11. 11
    Concentraciónconcentrated by rotary evaporation
12. 12
    Otrodried under high vacuum at ambient temperature

Procedimiento

Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethyoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, 18.3 mmol) in 1,2-dimethoxyethane (5 mL) was added. The mixture was stirred at ambient temperature for 3 days, cooled, and water (25 mL) was added dropwise. The mixture was diluted with water (200 mL) and extracted with chloroform (7×50 mL). All chloroform extracts were combined, dried (Na2 SO4), filtered, and concentrated by rotary evaporation. The residue was dried under high vacuum at ambient temperature to give a red-brown oil. The oil was chromatographed on silica gel (50 g), eluting with ethyl acetate. Selected fractions were combined, concentrated by rotary evaporation, and dried under high vacuum at ambient temperature to give compound V as a light yellow oil (0.40 g, 76.1%).

Fuente