반응 #76735

반응 방정식

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

수율 43.0%

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

수율 43.0%

용매

ethanol

ethyl acetate

tert-butanol

methyl sulfoxide

반응 조건

후처리

1. 1
   세척washed with water and brine
2. 2
   건조dried (MgSO4)
3. 3
   기타evaporated
4. 4
   workup.DISSOLUTIONThis material was dissolved in ethanol (70 mL)
5. 5
   workup.DISTILLATIONMost of the solvent was distilled off
6. 6
   기타the residue was partitioned between water and ether
7. 7
   세척The organic layer was washed with brine
8. 8
   건조dried (MgSO4)
9. 9
   기타evaporated

실험 절차

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.

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