Benzyl Bromide → 3-benzyl-6-bromoquinazolin-4(3H)-one

HRID 576584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 576584
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][NH:14][C:13]2=[O:20].[H-].[Na+]>CN(C=O)C>[CH2:1]([N:14]1[C:13](=[O:20])[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([Br:9])[CH:11]=2)[N:16]=[CH:15]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1354449056-bromoquinazolin-4-ol

Produkt 1

HCID 11875073-benzyl-6-bromoquinazolin-4(3H)-oneAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Benzyl bromide (0.264 mL, 2.22 mmol) was added to a solution of 6-bromoquinazolin-4(3H)-one (0.5 g, 2.22 mmol) and NaH (0.08 g, 3.33 mmol) in DMF (5 mL) at 0° C. The reaction mixture was heated to 80° C. for 4 h. The reaction mixture was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo to afford title compound (0.4 g, 48.1%) as pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.46 (d, J=1.6 Hz, 1H), 8.09 (s, 1H), 7.83 (dd, J1=2.0 Hz, J2=8.8 Hz, 1H), 7.57 (d, J=8.4 Hz, 1H), 7.4-7.2 (m, 5H), 5.2 (s, 2H); ESI-MS m/z=315 (M+H)+; LCMS purity: 84.2%

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customOrganic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-24e00efc82e24fb5a65e4025d99c2b86
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040517B2

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