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

HRID 711761Notes

Reaction equation

HRID 711761 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 251528124-amino-5-(methylamino)quinazolin-2(1H)-oneYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-474ebe9daace4a0695be7681de058eeb
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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