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Propylamine → 5,6-Dimethyl-2-(propylamino)-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

HRID 275907
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 275907
[CH2:1]([NH2:4])[CH2:2][CH3:3].C(N(CC)CC)C.[Cl:12][C:13]1[N:18]=[C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)[C:16]([CH3:29])=[C:15]([CH3:30])[N:14]=1>CN(C)C=O.ClCCl>[ClH:12].[CH3:29][C:16]1[C:17]([N:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20]2)=[N:18][C:13]([NH:4][CH2:1][CH2:2][CH3:3])=[N:14][C:15]=1[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7852PropylamineHCID 8471TriethylamineHCID 183157432-Chloro-5,6-dimethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Produkt 1

HCID 183157355,6-Dimethyl-2-(propylamino)-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Propylamine(0.44 g, 5.4 mmol) and triethylamine(0.38 ml, 2.7 mmol) were added to a mixture solution of 2-chloro-5,6-dimethyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine(0.5 g, 1.8 mmol) in dimethylformamide(10 ml). The reaction mixture was stirred for 5 hours at 130° C., cooled to a room temperature, diluted with dichloromethane, and then washed with aqueous sodium hydroxide and water. The separated organic layer was dried over anhydrous magnesium sulfate, concentrated under a reduced pressure, and then purified by column chromatography to give free base form of the titled compound. Ethyl ether saturated with hydrochloric acid was added to a mixture solution of the free base form of the titled compound in ethyl ether. The resulting solid was filtered and dried to obtain 490 mg of the titled compound.

Aufarbeitung

  1. temperaturecooled to a room temperature
  2. washwashed with aqueous sodium hydroxide and water
  3. dry with materialThe separated organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ba2d68a42ce449589a90e10308960f57
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06352993B1

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