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Hydrazine → 4-[[5-Amino4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile

HRID 1814911
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1814911
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11]1[C:16]([N+:17]([O-])=O)=[CH:15][N:14]=[C:13]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)[N:12]=1.NN>[Pd].C(O)C>[NH2:17][C:16]1[C:11]([NH:10][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=2[CH3:9])=[N:12][C:13]([NH:20][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)=[N:14][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 9321HydrazineHCID 221700954-[[4-[(2,4,6-Trimethylphenyl)amino]-5-nitro-2-pyrimidinyl]amino]benzonitrile

Produkt 1

HCID 221700874-[[5-Amino4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrileAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702Ethanol
Lösungsmittel

Versuchsvorschrift

4-[[4-[(2,4,6-trimethylphenyl)amino]-5-nitro-2-pyrimidinyl]amino]benzonitrile (0.001 mol), Pd/C 10% (0.025 g), ethanol (20 ml), and hydrazine (0.030 mol) were combined to form a slurry and stirred at room temperature for 16 hours. The solvent was removed by rotary evaporation. The residue was taken up in tetrahydrofuran (20 ml) and methanol (1 ml). A second portion of hydrazine (0.5 g) was added, and the reaction was stirred for 16 hours at room temperature. A third portion of hydrazine (0.5 ml) was added and the reaction was stirred for an additional 16 hours at room temperature. The sample was concentrated by rotary evaporation onto silica gel (1 g) and purified by flash chromatography (eluent: 0.5, 1,2% 10% (NH4OH in CH3OH) in CH2Cl2). The desired fractions were purified by preparatory HPLC to yield 0.24 g of 4-[[5-amino-4-[(2,4,6-trimethylphenyl)amino]-2-pyrimidinyl]amino]benzonitrile (70%); mp. 224-225° C. (comp. 51).

Aufarbeitung

  1. customto form a slurry
  2. customThe solvent was removed by rotary evaporation
  3. additionA second portion of hydrazine (0.5 g) was added
  4. stirringthe reaction was stirred for 16 hours at room temperature
  5. additionA third portion of hydrazine (0.5 ml) was added
  6. stirringthe reaction was stirred for an additional 16 hours at room temperature
  7. concentrationThe sample was concentrated by rotary evaporation onto silica gel (1 g)
  8. custompurified by flash chromatography (eluent: 0.5, 1,2% 10% (NH4OH in CH3OH) in CH2Cl2)
  9. customThe desired fractions were purified by preparatory HPLC

Quellen und Nachweise

ORD-Eintrag
ord-94c6517703cc4f41a654a4fc273ca025
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06878717B2

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