Reaktion #2814

Reaktionsgleichung

sodium hydride

IV

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

iodomethane

diisopropylamine

→

compound V

Ausbeute 76.1%

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

Ausbeute 76.1%

Lösungsmittel

water

1,2-dimethoxyethane

DMF

water

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   Temperaturcooled
3. 3
   Extraktionextracted with chloroform (7×50 mL)
4. 4
   Sonstigedried (Na2 SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated by rotary evaporation
7. 7
   SonstigeThe residue was dried under high vacuum at ambient temperature
8. 8
   Sonstigeto give a red-brown oil
9. 9
   SonstigeThe oil was chromatographed on silica gel (50 g)
10. 10
    Wascheneluting with ethyl acetate
11. 11
    Einengenconcentrated by rotary evaporation
12. 12
    Sonstigedried under high vacuum at ambient temperature

Vorschrift

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-dimethoxyethane (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%).

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