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

HRID 48455

Reaktionsgleichung

Reaktionsgleichung von HRID 48455
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]2[C:15]([NH2:21])=[N:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2COCC[Si](C)(C)C)[CH3:2].CC([O-])(C)C.[K+].C(OC1C=C(C=O)C=C2C=1C=CN2COCC[Si](C)(C)C)C.N(CCC#N)C1C=CC=CC=1.Cl.NC(N)=N>C(O)(C)(C)C.CS(C)=O.C(O)C.O>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([CH2:13][C:14]2[C:15]([NH2:21])=[N:16][C:17]([NH2:20])=[N:18][CH:19]=2)[CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH3:2]

Komponenten

10

Edukt 5

HCID 5742Guanidine HydrochlorideHCID 141003-AnilinopropionitrileHCID 227429264-ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-6-carbaldehydeHCID 23665647Potassium tert-butoxide2×HCID 699205545-[4-Ethoxy-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-ylmethyl]-pyrimidine-2,4-diamine

Produkt 1

HCID 227429195-(4-Ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-9540ad39a2414b7abb810eca8ddaf9f3
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703397B2

Verknüpfte Notizen

Wird geladen…