Diisopropylethylamine → HCID 22625087, Verbindung

HRID 279657Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279657
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][NH:16][CH3:17])[N:9]=[CH:8][N:7]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:6]2=[O:26].ClC1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=1.[CH:35](N(CC)C(C)C)(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]([CH3:35])[C:17]1[CH:33]=[C:32]([CH3:34])[N:31]=[CH:30][N:29]=1)[N:9]=[CH:8][N:7]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:23])([CH3:22])[CH3:24])[C:6]2=[O:26]

Komponenten

4

Edukt 3

HCID 81531DiisopropylethylamineHCID 5817964-Chloro-6-methylpyrimidineHCID 22624970HCID 22624970, Verbindung

Produkt 1

HCID 22625087HCID 22625087, VerbindungAusbeute 80 %

Versuchsvorschrift

A solution of 6-methoxy-7-(2-(methylamino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (363 mg, 1 mmol) and 4-chloro-6-methylpyrimidine (257 mg, 2 mmol), (J. Het. Chem., 1969, 6, 879), in N,N-diisopropylethylamine (2 ml) was heated at reflux for 30 minutes. The volatiles were removed by evaporation and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 6-methoxy-7-(2-(N-methyl-N-(6-methylpyrimidin-4-yl)amino)ethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (365 mg, 80%).

Aufarbeitung

  1. temperatureat reflux for 30 minutes
  2. customThe volatiles were removed by evaporation
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by column chromatography
  9. washeluting with methylene chloride/methanol (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-e9293f6bbc574701bb988bce2410e516
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362336B1

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