Réaction #1855

Équation de réaction

sodium hydride

IV

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

iodomethane

diisopropylamine

→

compound V

Rendement 76.1%

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

Rendement 76.1%

Solvants

water

1,2-dimethyoxyethane

DMF

water

1,2-dimethoxyethane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   Températurecooled
3. 3
   Extractionextracted with chloroform (7×50 mL)
4. 4
   Autredried (Na2 SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated by rotary evaporation
7. 7
   AutreThe residue was dried under high vacuum at ambient temperature
8. 8
   Autreto give a red-brown oil
9. 9
   AutreThe oil was chromatographed on silica gel (50 g)
10. 10
    Lavageeluting with ethyl acetate
11. 11
    Concentrationconcentrated by rotary evaporation
12. 12
    Autredried under high vacuum at ambient temperature

Mode opératoire

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%).

Source