Pyridine → 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[2-(3-cyano-2-methylguanidino)ethylthiomethyl]pyrimidine

HRID 364273

Reaktionsgleichung

Reaktionsgleichung von HRID 364273
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][CH2:10][CH2:11][NH:12][C:13]([NH:17][CH3:18])=[N:14][C:15]#[N:16])[N:3]=1.[F:19][C:20]([F:26])([F:25])[CH2:21][N:22]=[C:23]=S.[N:27]1C=CC=CC=1>>[F:19][C:20]([F:26])([F:25])[CH2:21][N:22]=[C:23]([NH2:27])[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][CH2:10][CH2:11][NH:12][C:13]([NH:14][C:15]#[N:16])=[N:17][CH3:18])[N:3]=1

Komponenten

4

Edukt 3

HCID 1049PyridineHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178485067HCID 178485067, Verbindung

Produkt 1

HCID 212988204-[2-(2,2,2-Trifluoroethyl)guanidino]-2-[2-(3-cyano-2-methylguanidino)ethylthiomethyl]pyrimidine

Versuchsvorschrift

A mixture of 4-amino-2-[2-(2-cyano-3-methylguanidino)ethylthiomethyl]pyrimidine (0.5 g.), 2,2,2-trifluoroethylisothiocyanate (0.55 g.) and pyridine (10 ml.) was heated at 70° for 18 hours and then evaporated to dryness. The residue was dissolved in ethyl acetate and the solution washed with 2N aqueous acetic acid, dried and evaporated to dryness. The residue was dissolved in ethanolic ammonia (15 ml.), treated with yellow mercuric oxide (0.4 g.) and the mixture stirred at room temperature for 4 hours. The mixture was filtered and the filtrate evaporated to dryness. The residue was purified by preparative thin layer chromatography using ethyl acetate/methanol/ammonia 6:1:0.5 v/v/v as developing solvent to give 4-[2-(2,2,2-trifluoroethyl)guanidino]-2-[2-(3-cyano-2-methylguanidino)ethylthiomethyl]pyrimidine (0.2 g.) characterised as the hydrogen maleate, m.p. 111°-114° (decomp.) after recrystallisation from acetonitrile.

Aufarbeitung

  1. temperaturewas heated at 70° for 18 hours
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution washed with 2N aqueous acetic acid
  5. customdried
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in ethanolic ammonia (15 ml.)
  8. additiontreated with yellow mercuric oxide (0.4 g.)
  9. filtrationThe mixture was filtered
  10. customthe filtrate evaporated to dryness
  11. customThe residue was purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-17241b7fe8cf46ab856f67f2a7d3a08e
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04604465

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