反应 #76735

反应方程式

guanidine hydrochloride

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

potassium tert-butylate

1-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indole-6-carbaldehyde

3-anilinopropionitrile

→

MeOH NH4OH

title compound

收率 43.0%

6-(2,4-Diamino-pyrimidin-5-ylmethyl)-1-methyl-1H-indol-4-ol

收率 43.0%

溶剂

ethanol

ethyl acetate

tert-butanol

methyl sulfoxide

反应条件

后处理

1. 1
   洗涤washed with water and brine
2. 2
   干燥dried (MgSO4)
3. 3
   其他evaporated
4. 4
   workup.DISSOLUTIONThis material was dissolved in ethanol (70 mL)
5. 5
   workup.DISTILLATIONMost of the solvent was distilled off
6. 6
   其他the residue was partitioned between water and ether
7. 7
   洗涤The organic layer was washed with brine
8. 8
   干燥dried (MgSO4)
9. 9
   其他evaporated

实验过程

5-[1-Methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine. A warm solution of potassium tert-butylate (2.68 g, 23.4 mmol) in tert-butanol (20 mL) was added to a room temperature solution of 1-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-1H-indole-6-carbaldehyde (5.95 g, 19.5 mmol) and 3-anilinopropionitrile (3.20 g, 21.4 mmol) in methyl sulfoxide (70 mL). After 2 h the solution was diluted with ethyl acetate, washed with water and brine, dried (MgSO4), and evaporated. This material was dissolved in ethanol (70 mL) and added to a suspension of guanidine hydrochloride (6.21 g, 64.4 mmol) in ethanol (210 mL), and the mixture was stirred at 70° C. for 22 h. Most of the solvent was distilled off, and the residue was partitioned between water and ether. The organic layer was washed with brine, dried (MgSO4), and evaporated. Flash chromatography (SiO2; CH2CL2/MeOH/NH4OH 19:1:0.05) afforded the title compound (3.32 g, 43%).Yellow solid.

来源