O-Toluidine → 6-Methoxymethyl-5-methyl-2-(2-methylphenylamino)-4-(1,2,3,4-tetrahydro isoquinolin-2-yl)pyrimidine hydrochloride

HRID 275931

Reaktionsgleichung

Reaktionsgleichung von HRID 275931
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:16][O:17][CH2:18][C:19]1[N:24]=[C:23]([Cl:25])[N:22]=[C:21]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)[C:20]=1[CH3:36]>CN(C)C=O.ClCCl>[ClH:25].[CH3:16][O:17][CH2:18][C:19]1[N:24]=[C:23]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH3:8])[N:22]=[C:21]([N:26]2[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]2)[C:20]=1[CH3:36]

Komponenten

6

Edukt 3

HCID 7242O-ToluidineHCID 8471TriethylamineHCID 183157876-Methoxymethyl-5-methyl-2-chloro-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine

Produkt 1

HCID 183158106-Methoxymethyl-5-methyl-2-(2-methylphenylamino)-4-(1,2,3,4-tetrahydro isoquinolin-2-yl)pyrimidine hydrochlorideAusbeute 32,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

o-Toluidine(0.48 ml, 4.5 mmol) and triethylamine were added to a solution of 6-methoxymethyl-5-methyl-2-chloro-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)pyrimidine (0.9 g, 3 mmol) in dimethylformamide(5 ml) and stirred for 5 hours at 130° C. The reaction mixture was cooled to a room temperature, diluted with dichloromethane, and washed with aqueous sodium hydroxide and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the residual oil was purified by column chromatography. The purified compound was dissolved in ethyl ether. Ethyl ether saturated with hydrochloric acid was added to a mixture solution. The resulting solid was filtered and dried to give 400 mg of the titled compound.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to a room temperature
  2. washwashed with aqueous sodium hydroxide and water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe residual oil was purified by column chromatography
  6. dissolutionThe purified compound was dissolved in ethyl ether
  7. additionEthyl ether saturated with hydrochloric acid was added to a mixture solution
  8. filtrationThe resulting solid was filtered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-305f6026270e46898cae1cd4b3176bc2
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352993B1

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