Triethylamine → 2,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide

HRID 1616123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616123
[O:1]=[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([C:13]([OH:15])=O)=[CH:7][CH:8]=2)[NH:3]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.FC(N(C)C)=[N+](C)C.[O:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH:39]1[O:44][NH2:45]>O.CN(C=O)C>[O:1]=[C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][C:6]([C:13]([NH:45][O:44][CH:39]3[CH2:40][CH2:41][CH2:42][CH2:43][O:38]3)=[O:15])=[CH:7][CH:8]=2)[NH:3]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2774761Tetramethylfluoroformamidinium hexafluorophosphateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 196042892,4-Dihydroxyquinazoline-7-carboxylic acid

Produkt 1

HCID 866642012,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamideAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carboxylic acid (0.15 g, 0.73 mmol), DMF (2.80 mL), triethylamine (0.30 mL, 2.2 mmol) and fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate (0.25 g, 0.95 mmol) was stirred for 15 min and O-(tetrahydropyran-2-yl)hydroxylamine (0.10 g, 0.87 mmol) was added. The reaction mixture was stirred at rt for 1 d. Water was added and the mixture was extracted with EtOAc (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes) to afford 2,4-dioxo-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroquinazoline-7-carboxamide (0.15 g, 68%). LC-MS: (FA) ES+ 306.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at rt for 1 d
  2. extractionthe mixture was extracted with EtOAc (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (50% to 100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-69ef4a07c99641daae4a46b6e765bad0
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765773B2

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