反应 #1855

反应方程式

sodium hydride

IV

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

iodomethane

diisopropylamine

→

compound V

收率 76.1%

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

收率 76.1%

溶剂

water

1,2-dimethyoxyethane

DMF

water

1,2-dimethoxyethane

反应条件

后处理

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

实验过程

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%).

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