N,N-Dimethylaniline → 4-chloro-N-(3-chlorophenyl)pyrimidin-2-amine

HRID 1692990

Reaktionsgleichung

Reaktionsgleichung von HRID 1692990
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[NH:14][C:13](=O)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:27])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:27][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:14]=1

Komponenten

6

Edukt 4

HCID 949N,N-DimethylanilineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 16392332-(3-chlorophenylamino)pyrimidin-4(3H)-one

Produkt 1

HCID 590282434-chloro-N-(3-chlorophenyl)pyrimidin-2-amineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To 2-(3-chlorophenylamino)pyrimidin-4(3H)-one, 2, (3.00 g, 13.5 mmol) in toluene (30 mL) is added N,N-dimethyl-aniline (3.57 mL, 28.4 mmol) and phosphorus oxychloride (1.24 mL, 13.5 mmol). The resulting mixture is heated to reflux for 15 minutes, cooled to room temperature and neutralized to pH 7 with 1M NaOH (aqueous). The organic layer is extracted with EtOAc (3×250 mL). The combined organic layers are dried (MgSO4) and concentrated in vacuo. The residue is purified over silica (5% EtOAc in hexanes) to afford 2.0 g (61% yield) of the desired compound. 1H NMR (DMSO-d6, 300 MHz): δ 7.06-7.04 (m, 2H), 7.34 (t, J=8.1, 1H), 7.65-7.61 (m, 1H), 7.93 (m, 1H), 8.50 (d, J=5.1 Hz, 1H), 10.26 (s, 1H).

Aufarbeitung

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 15 minutes
  3. extractionThe organic layer is extracted with EtOAc (3×250 mL)
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified over silica (5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a161c0b9f7964422aeaae489c9b6d890
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158641B2

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