Реакция #80684

Уравнение реакции

sodium hydride

IV

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

iodomethane

diisopropylamine

→

compound V

Выход 76.1%

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

Выход 76.1%

Растворители

water

1,2-dimethoxyethane

DMF

water

1,2-dimethoxyethane

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   Температураcooled
3. 3
   Экстракцияextracted with chloroform (7×50 mL)
4. 4
   Сушкаdried (Na2SO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated by rotary evaporation
7. 7
   ДругоеThe residue was dried under high vacuum at ambient temperature
8. 8
   Другоеto give a red-brown oil
9. 9
   ДругоеThe oil was chromatographed on silica gel (50 g)
10. 10
    Промывкаeluting with ethyl acetate
11. 11
    Концентрированиеconcentrated by rotary evaporation
12. 12
    Другоеdried under high vacuum at ambient temperature

Методика

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 (Na2SO4), 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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