2-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine → Imatinib amine

HRID 562574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562574
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[N:17]=[C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH:15]=[CH:14][N:13]=1>C(OCC)(=O)C.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[CH:15]=[CH:14][N:13]=2)[CH:4]=1

Komponenten

4

Edukt 1

HCID 106861492-(2-Methyl-5-nitroanilino)-4-(3-pyridyl)pyrimidine

Produkt 1

HCID 9965429Imatinib amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 143.0 g (0.46 mol) of N-(2-methyl-5-nitrophenyl)-4-(3-pyridyl)-2-pyrimidine-amine in 7.15 liters of ethyl acetate is stirred with 14.3 g of palladium on active carbon (10% Pd) under a hydrogen atmosphere at normal pressure for 6.5 hours. The suspension is filtered and the filtrate is concentrated in a rotary evaporator. The crude product is recrystallised from methylene chloride, yielding N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidine-amine; m.p. 138° C.-140° C., Rf=0.36 (methylene chloride:methanol=9:1).

Aufarbeitung

  1. filtrationThe suspension is filtered
  2. concentrationthe filtrate is concentrated in a rotary evaporator
  3. customThe crude product is recrystallised from methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-4ee40fbc998a47f389b8ecbc97d0cfa7
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067421B2

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