반응 #57387

반응 방정식

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

수율 24.0%

용매

acetone MeCN

DMF

DMF

EA THF

water

DMF

반응 조건

후처리

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
   기타The organic phase was separated off
4. 4
   추출the aq. phase was extracted with EA
5. 5
   건조The combined organic phases were dried over MgSO4
6. 6
   여과filtered
7. 7
   기타evaporated under a vacuum

실험 절차

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).

출처