反应 #76733

反应方程式

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

收率 62.0%

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

收率 62.0%

溶剂

water

ethanol

tert-butanol

methyl sulfoxide

反应条件

后处理

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

实验过程

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.

来源