Triethylamine → 2-methyl-5-(7-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamine

HRID 2294011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294011
Cl[CH2:2][C:3]1[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=1.C(N(CC)CC)C.[C:18]1([C:24]2[CH:33]=[C:32]3[C:27]([CH2:28][CH2:29][NH:30][CH2:31]3)=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O>[CH3:9][C:6]1[N:5]=[C:4]([NH2:10])[C:3]([CH2:2][N:30]2[CH2:29][CH2:28][C:27]3[C:32](=[CH:33][C:24]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)=[CH:25][CH:26]=3)[CH2:31]2)=[CH:8][N:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 324007-Phenyl-1,2,3,4-tetrahydroisoquinolineHCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidine

Produkt 1

HCID 214736992-methyl-5-(7-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 0.17 g (0.00088 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 10 ml of dimethylformamide was treated with 0.30 ml (0.0021 mol) of triethylamine and 0.184 g (0.00088 mol) of 7-phenyl-1,2,3,4-tetrahydro-isoquinoline and the mixture was stirred at room temperature under argon for 18 hours. The solvent was distilled off in a high vacuum. The residue was partitioned between dichloromethane/water, extracted and dried over MgSO4. After removing the solvent the residue was chromatographed over silica gel with ethyl acetate as the eluent. 0.22 g (76%) of 2-methyl-5-(7-phenyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-pyrimidin-4-ylamine was obtained as a light yellowish solid; m.p. 147°-149°.

Aufarbeitung

  1. distillationThe solvent was distilled off in a high vacuum
  2. customThe residue was partitioned between dichloromethane/water
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent the residue
  6. customwas chromatographed over silica gel with ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-ccd32a52a53c4457a4e475fcb3e7686e
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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