Sodium Hydroxide → 2-pyrimidinamine, N-(3-chlorophenyl)-4-(4-pyridinyl)-

HRID 724822

Reaktionsgleichung

Reaktionsgleichung von HRID 724822
[N+]([O-])(O)=O.[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([NH2:15])=[NH:14])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+].CN(C)[CH:20]=[CH:21][C:22]([C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1)=O>C(O)C(C)C>[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[N:15]=[C:22]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)[CH:21]=[CH:20][N:14]=2)[CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 178512489HCID 178512489, Verbindung

Produkt 1

HCID 6442142-pyrimidinamine, N-(3-chlorophenyl)-4-(4-pyridinyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6560IsobutanolLösungsmittel

Versuchsvorschrift

2.8 g (12 mmol) of 3-chloro-phenyl-guanidine nitrate and 0.5 g (12 mmol) of sodium hydroxide are added to a suspension of 2.0 g (11.7 mmol) of 3-dimethylamino-1-(4-pyridyl)-2-propen-1-one [described in EP-A-0 233 461] in 100 ml of isobutanol and the reaction mixture is boiled under reflux for 5 hours. After cooling, the reaction product is isolated by filtration, washed with water and chromatographed (tetrahydrofuran). After crystallisation (tetrahydrofuran/diethyl ether), N-(3-chloro-phenyl)-4-pyridyl-2-pyrimidineamine is obtained; m.p. 167°-168°, Rf =0.38 (methylene chloride:methanol=9:1).

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter cooling
  3. customthe reaction product is isolated by filtration
  4. washwashed with water
  5. customchromatographed (tetrahydrofuran)
  6. customAfter crystallisation (tetrahydrofuran/diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-807c46245b414f2a8ee61321bce0326e
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705502

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