Reaction #76733
ord-9540ad39a2414b7abb810eca8ddaf9f3
Reaction equation
Reactants
Reagents
Conditions
Workup
- 1Otherthe suspension formed
- 2FiltrationThe precipitate was collected by filtration
- 3Otherdried
- 4Temperaturethe reaction mixture was refluxed for 16 h
- 5workup.DISTILLATIONmost of the solvent was distilled off
- 6workup.ADDITIONether (50 mL) was added
- 7OtherInsoluble material was removed by filtration
- 8Washthe filtrate was washed with water
- 9Dryingdried (MgSO4)
- 10Otherevaporated
- 11WashThe residue was washed with diethyl ether/n-hexane 4:3 (70 mL)
Procedure
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.