반응 #1855

반응 방정식

sodium hydride

IV

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

iodomethane

diisopropylamine

→

compound V

수율 76.1%

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

수율 76.1%

용매

water

1,2-dimethyoxyethane

DMF

water

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   온도cooled
3. 3
   추출extracted with chloroform (7×50 mL)
4. 4
   기타dried (Na2 SO4)
5. 5
   여과filtered
6. 6
   농축concentrated by rotary evaporation
7. 7
   기타The residue was dried under high vacuum at ambient temperature
8. 8
   기타to give a red-brown oil
9. 9
   기타The oil was chromatographed on silica gel (50 g)
10. 10
    세척eluting with ethyl acetate
11. 11
    농축concentrated by rotary evaporation
12. 12
    기타dried under high vacuum at ambient temperature

실험 절차

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%).

출처