1,2,3,4-Tetrahydroisoquinoline → 6-Methoxymethyl-5-methyl-2-chloro-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

HRID 275930

Reaktionsgleichung

Reaktionsgleichung von HRID 275930
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.[Cl:11][C:12]1[N:17]=[C:16](Cl)[C:15]([CH3:19])=[C:14]([CH2:20][O:21][CH3:22])[N:13]=1.C(N(CC)CC)C>CN(C)C=O.ClCCl>[CH3:22][O:21][CH2:20][C:14]1[N:13]=[C:12]([Cl:11])[N:17]=[C:16]([N:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)[C:15]=1[CH3:19]

Komponenten

6

Edukt 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471TriethylamineHCID 183158422,4-Dichloro-6-methoxymethyl-5-methylpyrimidine

Produkt 1

HCID 183157876-Methoxymethyl-5-methyl-2-chloro-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidineAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,2,3,4-tetrahydroisoquinoline(0.9 ml, 6.9 mmol) was added dropwise to a solution of 2,4-dichloro-6-methoxymethyl-5-methylpyrimidine(1.3 g, 6.3 mmol) and triethylamine(0.96 ml, 6.9 mmol) in dimethylformamide and stirred for 5 hours at a room temperature. The reaction mixture was diluted with dichloromethane and washed with water and aqueous sodium hydroxide solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure. The resulting residue was purified by a silica gel column chromatography to give 1.8 g of the titled compound. (Yield: 94.0%)

Aufarbeitung

  1. washwashed with water and aqueous sodium hydroxide solution
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe resulting residue was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1dbbe70370ea45ecafc7c35a3178b8a0
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352993B1

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