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

HRID 2294012

Reaktionsgleichung

Reaktionsgleichung von HRID 2294012
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.[CH2:18]([O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH2:30][CH2:31][NH:32][CH2:33]2)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH2:30][CH2:31][N:32]([CH2:2][C:3]3[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=3)[CH2:33]2)=[CH:28][CH:27]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidineHCID 214630147-(Benzyloxy)-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 214736855-(7-benzyloxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamineAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 0.23 g (0.0012 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 10 ml of dimethylformamide was treated with 0.42 ml (0.0030 mol) of triethylamine and 0.29 g (0.0012 mol) of 7-benzyloxy-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 on silica gel with ethyl acetate as the eluent. 0.22 g (51%) of 5-(7-benzyloxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine was obtained as a colourless solid; m.p. 151°-153°.

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 on silica gel with ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-378920fcdbcd4390a64190d968976ed5
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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