1-Methylpiperazine → 6-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

HRID 855710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855710
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:24])[N:11]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:25][CH3:26].[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1>>[CH3:26][O:25][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:6]=1[O:5][CH2:4][CH2:3][CH2:2][N:31]1[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]1)[N:13]=[CH:12][N:11]([CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]2=[O:24]

Komponenten

3

Edukt 2

HCID 531671-MethylpiperazineHCID 179427567-(3-Chloropropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one

Produkt 1

HCID 220306066-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-oneAusbeute 92 %

Versuchsvorschrift

A solution of 7-(3-chloropropoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (3 g, 7.84 mmol) in 1-methylpiperazine (30 ml) was heated at 100° C. for 1 hour. After cooling, the mixture was partitioned between saturated ammonium chloride and methylene chloride. The organic layer was washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5 followed by 90/10). The volatiles were removed by evaporation to give 6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (3.24 g, 92%).

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe mixture was partitioned between saturated ammonium chloride and methylene chloride
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customthe volatiles were removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with methylene chloride/methanol (95/5 followed by 90/10)
  8. customThe volatiles were removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-cd08d6e710564d7aba4312677a858e69
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262201B1

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