Isopropanol → [4-(5-Chloro-thiazol-2-yl)-pyrimidin-2-yl]-(3,4,5-trimethoxy-phenyl)-amine

HRID 1178208

Reaktionsgleichung

Reaktionsgleichung von HRID 1178208
[Cl:1][C:2]1[S:6][C:5]([CH:7]=[CH:8]N(C)C)=[N:4][CH:3]=1.[N+]([O-])([O-])=O.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([NH:28][C:29]([NH2:31])=[NH2+:30])[CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25].[OH-].[Na+].[CH:34](O)(C)C>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:34][N:31]=[C:29]([NH:28][C:20]3[CH:21]=[C:22]([O:26][CH3:27])[C:23]([O:24][CH3:25])=[C:18]([O:17][CH3:16])[CH:19]=3)[N:30]=2)=[N:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 72478490[2-(5-Chloro-thiazol-2-yl)-vinyl]-dimethyl-amineHCID 178419082HCID 178419082, Verbindung

Produkt 1

HCID 58974673[4-(5-Chloro-thiazol-2-yl)-pyrimidin-2-yl]-(3,4,5-trimethoxy-phenyl)-amineAusbeute 35 %

Versuchsvorschrift

To a solution of [2-(5-Chloro-thiazol-2-yl)-vinyl]-dimethyl-amine (450 mg) in isopropanol (10 ml) was added N-(3,4,5 trimethoxyphenyl)guanidinium nitrate (560 mg) (prepared using a procedure similar to that described in WO9719065) and sodium hydroxide (80 mg). The resulting mixture was heated to reflux for 6 hours, then cooled to ambient and concentrated. The mixture was diluted with water (20 ml) and extracted with ethylacetate (20 ml), the organic phase was removed, washed with water, brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography (30% ethylacetate/petroleum ether) to afford the sub-titled compound as an orange solid (260 mg, 35%); IR (solid) 1570, 1508, 1453, 1422 cm−1; 1H NMR (400 Mhz, CDClS) δ 3.8 (3H, s), 3.95 (6H, s), 7.15 (1H, s), 7.50 (1H, m), 7.75 (1H, s), 8.6 (1H, d); MS (ES+) 379.2 (M+1), (ES−) 377.2 (M−1).

Aufarbeitung

  1. customprepared
  2. temperatureThe resulting mixture was heated
  3. temperatureto reflux for 6 hours
  4. temperaturecooled to ambient and
  5. concentrationconcentrated
  6. additionThe mixture was diluted with water (20 ml)
  7. extractionextracted with ethylacetate (20 ml)
  8. customthe organic phase was removed
  9. washwashed with water, brine
  10. dry with materialdried (magnesium sulfate)
  11. concentrationconcentrated
  12. customThe residue was purified by flash chromatography (30% ethylacetate/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-32f88d911b28453aaaff0285f49fc22e
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276502B2

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