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

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.

1. customthe suspension formed
2. filtrationThe precipitate was collected by filtration
3. customdried
4. temperaturethe reaction mixture was refluxed for 16 h
5. distillationmost of the solvent was distilled off
6. additionether (50 mL) was added
7. customInsoluble material was removed by filtration
8. washthe filtrate was washed with water
9. dry with materialdried (MgSO4)
10. customevaporated
11. washThe residue was washed with diethyl ether/n-hexane 4:3 (70 mL)

ORD record

ord-9540ad39a2414b7abb810eca8ddaf9f3

Source dataset

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06703397B2