反応 #76733

反応方程式

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

収率 62.0%

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

収率 62.0%

溶媒

water

ethanol

tert-butanol

methyl sulfoxide

反応条件

後処理

1. 1
   その他the suspension formed
2. 2
   ろ過The precipitate was collected by filtration
3. 3
   その他dried
4. 4
   温度the 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
   その他Insoluble material was removed by filtration
8. 8
   洗浄the filtrate was washed with water
9. 9
   乾燥dried (MgSO4)
10. 10
    その他evaporated
11. 11
    洗浄The residue was washed with diethyl ether/n-hexane 4:3 (70 mL)

実験手順

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.

出典