Реакция #57387

Уравнение реакции

sodium hydride

methyl iodide

sodium hydride

tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

Na2CO3

methyl iodide

→

N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

Выход 24.0%

Растворители

acetone MeCN

DMF

DMF

EA THF

water

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture stirred at RT for a further 16 h
2. 2
   workup.STIRRINGthe mixture stirred at RT for a further 16 h
3. 3
   ДругоеThe organic phase was separated off
4. 4
   Экстракцияthe aq. phase was extracted with EA
5. 5
   СушкаThe combined organic phases were dried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated under a vacuum

Методика

43 mg (1.08 mmol, 60% in mineral oil) of sodium hydride were added to a solution of 135 mg (0.36 mmol) of tert-butyl-[2-(5-pyridin-2-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (Example 77) in DMF (3 ml) and the mixture was stirred at RT for 1 h. A solution of 67 μl (1.08 mmol) of methyl iodide in DMF (500 μl) was then added dropwise thereto and the mixture stirred at RT for a further 16 h. A further 43 mg (1.08 mmol, 60% in mineral oil) of sodium hydride and a solution of 67 μl (1.08 mmol) of methyl iodide in DMF (500 μl) were then added and the mixture stirred at RT for a further 16 h. The reaction solution was combined in succession with water, a 1M aq. Na2CO3 solution and a mixture of EA/THF (3:1). The organic phase was separated off and the aq. phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered and evaporated under a vacuum. 33 mg (0.09 mmol, 24%) of N-tert-butyl-N-methyl-2-(5-(pyridin-2-ylethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (acetone/MeCN 1:1).

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