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

HRID 2294013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2294013
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]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][NH:30][CH2:31]2)[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]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][N:30]([CH2:2][C:3]1[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=1)[CH2:31]2)[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 214736435-Benzyloxy-1,2,3,4-tetrahydro-isoquinoline

Produkt 1

HCID 214736835-(5-benzyloxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 0.098 g (0.00051 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 2 ml of dimethylformamide was treated with 0.21 ml (0.0015 mol) of triethylamine and 0.145 g (0.00061 mol) of 5-benzyloxy-1,2,3,4-tetrahydro-isoquinoline (WO 94/20459) 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 dichloro-methane/water, extracted and dried over MgSO4. After removing the solvent the residue was chromatographed on silica gel with ethyl acetate as the eluent. 0.153 g (84%) of 5-(5-benzyloxy-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-2-methyl-pyrimidin-4-ylamine was obtained as a yellowish oil. MS (ISP): me/e=361 (C22 H25N4O+).

Aufarbeitung

  1. distillationwas distilled off in a high vacuum
  2. customThe residue was partitioned between dichloro-methane/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-7d7ec4d4c5cc4285b7a6cf841894ca8e
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05688798

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