2,4-Pentanedione, 3-benzyl- → 4-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

HRID 1410391

Reaktionsgleichung

Reaktionsgleichung von HRID 1410391
[NH:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH2:15])[N:4]=1)[NH2:2].[CH2:16]([CH:23]([C:27](=O)[CH3:28])[C:24](=O)[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O.C(Cl)Cl.C(OCC)(=O)C>[CH2:16]([C:23]1[C:24]([CH3:25])=[N:2][N:1]([C:3]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=3)[N:6]=[C:5]([NH2:15])[N:4]=2)[C:27]=1[CH3:28])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

7

Edukt 3

HCID 977572,4-Pentanedione, 3-benzyl-HCID 521998p-Toluenesulfonic acid monohydrateHCID 6089524-Hydrazinyl-6-(pyridin-2-yl)-1,3,5-triazin-2-amine

Produkt 1

HCID 221748704-(4-Benzyl-3,5-dimethyl-pyrazol-1-yl)-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A suspension of 4-hydrazino-6-pyridin-2-yl-[1,3,5]triazin-2-ylamine (5.25 g, 25.6 mmol), 3-benzylpentane-2,4-dione (5.0 g, 28.4 mmol), and p-toluenesulfonic acid monohydrate (0.475 g, 2.50 mmol) in dimethylsulfoxide (50 mL) was heated to 75° C. for 20 hours. The reaction mixture was allowed to cool to room temperature, and the suspension was dissolved in methylene chloride (700 mL). The solution was washed three times with water, once with brine, dried (magnesium sulfate), and concentrated to afford a moist solid. The crude product was suspended in ethyl acetate (50 mL), heated to reflux, allowed to cool to room temperature, and filtered (repeated three times). The final product was obtained as a white solid containing 3% dimethylsulfoxide by weight: 8.63 g (90%). 1H NMR (CDCl3) δ 8.84-8.53 (m, 1H), 8.48 (d, J=7.9 Hz, 1H), 7.86-7.91 (m, 1H), 7.46-7.50 (m, 1H), 7.13-7.30 (m, 5H), 6.61 (br s, 1H), 6.40 (br s, 1H), 3.83 (s, 2H), 2.79 (s, 3H), 2.24 (s, 3H) ppm. MS (ESI) m/z 358 (M+H+).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washThe solution was washed three times with water
  3. dry with materialonce with brine, dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customto afford a moist solid
  6. temperatureheated
  7. temperatureto reflux
  8. temperatureto cool to room temperature
  9. filtrationfiltered (repeated three times)

Quellen und Nachweise

ORD-Eintrag
ord-0ec59d321b824d4aa36ef231c649cb12
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921547B2

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