Sodium Hydroxide → 4-amino-5-(methylamino)quinazolin-2(1H)-one

HRID 711761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 711761
[C:1]([C:3]1[C:8]([NH:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[NH:11][C:12]([NH:14]C(=O)C1C=CC=CC=1)=[O:13])#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[NH:9][CH3:10])[NH:11][C:12](=[O:13])[N:14]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 67401506N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide

Produkt 1

HCID 251528124-amino-5-(methylamino)quinazolin-2(1H)-oneAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide (Example 157a) (0.05 g, 0.17 mmol) and NaOH (2N, 0.17 mL) in EtOH (6 mL) was stirred at 90° C. under nitrogen for half an hour. The reaction mixture was cooled down to room temperature, and concentrated under vacuum. H2O (1 mL) was added and the reaction mixture was neutralized to pH˜4 with 10% AcOH. The resultant precipitation was filtered and dried under vacuum. The crude product was purified by preparative thin layer chromatography using a DCM/MeOH (9:1) solution as eluant, to give 4-amino-5-(methylamino)quinazolin-2(1H)-one (18.2 mg, 56%). 1H NMR (400 MHz, DMSO-d6) δ 2.76 (s, 3H), 6.10 (d, J=7.6 Hz, 1H), 6.12 (d, J=8 Hz, 1H), 7.13 (t, J=8 Hz, 1H), 7.25 (bs, NH), 9.66 (bs, NH) 10.13 (bs, 2H). MS 191 (MH+).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. additionH2O (1 mL) was added
  3. customThe resultant precipitation
  4. filtrationwas filtered
  5. customdried under vacuum
  6. customThe crude product was purified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-474ebe9daace4a0695be7681de058eeb
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181276B2

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