Triethylamine → 5,6-Dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 275947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275947
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][C:17]1[C:18]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][C:29]([OH:36])=[C:30]([OH:35])[CH:31]=3)[CH:26]2[CH3:37])=[N:19][C:20]([Cl:24])=[N:21][C:22]=1[CH3:23].[OH-].[Na+]>ClCCl>[ClH:24].[CH3:16][C:17]1[C:18]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][C:29]([OH:36])=[C:30]([OH:35])[CH:31]=3)[CH:26]2[CH3:37])=[N:19][C:20]([NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)=[N:21][C:22]=1[CH3:23]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 97314-FluoroanilineHCID 14798Sodium HydroxideHCID 183156425,6-Dimethyl-2-chloro-4-(1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Produkt 1

HCID 183157675,6-Dimethyl-2-(4-fluorophenylamino)-4-(1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochlorideAusbeute 39,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-fluoroaniline(0.46 ml, 4.70 mmol) and triethylamine(0.66 ml, 4.70 mmol) were added to a solution of 5,6-dimethyl-2-chloro-4-(1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(1.0 g, 3.13 mmol) in dimethyifomiamide(5 ml) and then stirred for 3 hours at 120° C. The reaction mixture was cooled to a room temperature and diluted with dichloromethane. Aqueous sodium hydroxide solution was added to the reaction mixture, which was then stirred. The dichloromethane layer was dried over anhydrous magnesium sulfate, concentrated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography and dissolved in ethanol. Ethyl ether saturated with hydrochloric acid was added to the solution. The resulting solid was filtered and dried to give 530 mg of the titled compound.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to a room temperature
  2. stirringwas then stirred
  3. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting residue was purified by a silica gel column chromatography
  6. dissolutiondissolved in ethanol
  7. additionEthyl ether saturated with hydrochloric acid was added to the solution
  8. filtrationThe resulting solid was filtered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-fc71dce9d64347e8946127750024bf2e
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352993B1

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