Triethylamine → 5,6-Dimethyl-2-chloro4-(6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

HRID 275940

Reaktionsgleichung

Reaktionsgleichung von HRID 275940
[CH3:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.C(N(CC)CC)C.[CH3:21][C:22]1[C:23](Cl)=[N:24][C:25]([Cl:29])=[N:26][C:27]=1[CH3:28]>CN(C)C=O.C(OCC)(=O)C>[CH3:21][C:22]1[C:23]([N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=3)[CH:2]2[CH3:1])=[N:24][C:25]([Cl:29])=[N:26][C:27]=1[CH3:28]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 2415532,4-Dichloro-5,6-dimethylpyrimidineHCID 142302816-Methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 183156315,6-Dimethyl-2-chloro4-(6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidineAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

After 1-methyl-6-methoxy-1,2,3,4-tetrahydroisoquinoline(1.3 g, 7.3 mmol) and triethylamine(1.0 ml, 7.3 mmol) were added to a suspension of 5,6-dimethyl-2,4-dichloropyrimidine(1.2 g, 6.64 mmol) in dimethylformamide, the reaction mixture was stirred for 3 hours at 85° C. The reaction mixture was cooled to a room temperature and diluted with ethyl acetate. The organic layer was washed with water and aqueous sodium hydroxide, dried over anhydrous magnesium sulfate, concentrated under a reduced pressure, and then purified by a silica gel column chromatography to give 1.7 g of the titled compound. (Yield: 78.5%)

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to a room temperature
  2. washThe organic layer was washed with water and aqueous sodium hydroxide
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. custompurified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6a299d49c56b4a55b2c4f611164c0410
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352993B1

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