反応 #1855

反応方程式

sodium hydride

IV

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

iodomethane

diisopropylamine

→

compound V

収率 76.1%

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

収率 76.1%

溶媒

water

1,2-dimethyoxyethane

DMF

water

1,2-dimethoxyethane

反応条件

後処理

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   温度cooled
3. 3
   抽出extracted with chloroform (7×50 mL)
4. 4
   その他dried (Na2 SO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated by rotary evaporation
7. 7
   その他The residue was dried under high vacuum at ambient temperature
8. 8
   その他to give a red-brown oil
9. 9
   その他The oil was chromatographed on silica gel (50 g)
10. 10
    洗浄eluting with ethyl acetate
11. 11
    濃縮concentrated by rotary evaporation
12. 12
    その他dried under high vacuum at ambient temperature

実験手順

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%).

出典