반응 #76733

반응 방정식

5-[4-Ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine

guanidine hydrochloride

potassium tert-butylate

potassium tert-butylate

4-ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-6-carbaldehyde

3-anilinopropionitrile

→

title compound

수율 62.0%

5-(4-Ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine

수율 62.0%

용매

water

ethanol

tert-butanol

methyl sulfoxide

반응 조건

후처리

1. 1
   기타the suspension formed
2. 2
   여과The precipitate was collected by filtration
3. 3
   기타dried
4. 4
   온도the reaction mixture was refluxed for 16 h
5. 5
   workup.DISTILLATIONmost of the solvent was distilled off
6. 6
   workup.ADDITIONether (50 mL) was added
7. 7
   기타Insoluble material was removed by filtration
8. 8
   세척the filtrate was washed with water
9. 9
   건조dried (MgSO4)
10. 10
    기타evaporated
11. 11
    세척The residue was washed with diethyl ether/n-hexane 4:3 (70 mL)

실험 절차

5-[4-Ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine. A warm solution of potassium tert-butylate (900 mg, 8.02 mmol) in tert-butanol (7.5 mL) was added at room temperature to a solution of 4-ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-6-carbaldehyde (2.14 g, 6.69 mmol) and 3-anilinopropionitrile (1.08 g, 7.36 mmol) in methyl sulfoxide (25 mL). After 90 min the solution was treated with water and the suspension formed was stirred for 2 h. The precipitate was collected by filtration and dried. This material was added to a suspension of guanidine hydrochloride (1.90 g, 19.9 mmol) and potassium tert-butylate (2.23 g, 19.9 mmol) in ethanol (100 mL), and the reaction mixture was refluxed for 16 h, then most of the solvent was distilled off, and ether (50 mL) was added. Insoluble material was removed by filtration, the filtrate was washed with water, dried (MgSO4), and evaporated. The residue was washed with diethyl ether/n-hexane 4:3 (70 mL) to afford the title compound (1.71 g, 62%). Light brown solid.

출처