Triethylamine → 5-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine

HRID 2294010

Reaktionsgleichung

Reaktionsgleichung von HRID 2294010
Cl.Cl[CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1.C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH2:27][NH:26][CH2:25][CH2:24]2>CN(C)C=O>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH2:27][N:26]([CH2:3][C:4]1[C:5]([NH2:11])=[N:6][C:7]([CH3:10])=[N:8][CH:9]=1)[CH2:25][CH2:24]2

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 214736115-(Chloromethyl)-2-methylpyrimidin-4-amine--hydrogen chloride (1/1)

Produkt 1

HCID 214736985-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamineAusbeute 22,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 0.80 g (0.00412 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine hydrochloride in 17 ml of dimethylformamide was treated with 1.7 ml (0.0124 mol) of triethylamine and 0.87 g (0.0053 mol) of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline and the mixture was stirred at room temperature under argon for 3 hours. The mixture was completely freed from the solvents and the residue was triturated in 20 ml of water. The resulting crystals were filtered off under suction, chromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent and recrystallized from ethyl acetate/n-hexane. 0.26 g (22%) of 5-(6-methoxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine was obtained as white crystals; m.p. 142°-143°.

Aufarbeitung

  1. customthe residue was triturated in 20 ml of water
  2. filtrationThe resulting crystals were filtered off under suction
  3. customchromatographed over silica gel with dichloromethane/methanol 9:1 as the eluent
  4. customrecrystallized from ethyl acetate/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-49d977aebe9445428ad63540d468cc9e
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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