N,N-Dimethylaniline → (6-Bromo-4-chloro-quinazolin-2-yl)-methyl-amine

HRID 1783632Notes

Reaction equation

HRID 1783632 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([NH:12][CH3:13])=[N:6][C:5]2=O.CN(C)C1C=CC=CC=1.[OH-].[Na+].P(Cl)(Cl)([Cl:28])=O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH3:13])[N:6]=[C:5]2[Cl:28]

Participants

5

Reactant 4

HCID 949N,N-DimethylanilineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178482429HCID 178482429, compound

Product 1

HCID 57590623(6-Bromo-4-chloro-quinazolin-2-yl)-methyl-amineYield 46.6%

Procedure

To a solution of phosphorus oxychloride (50 mL) was added powdered 6-bromo-2-methylamino-1H-quinazolin-4-one (10.0 g, 39.4 mmol) followed by dimethyl-phenyl-amine (8 mL) and the mixture was heated to reflux under N2 atmosphere for half an hour. After cooling down, the mixture was poured onto ice and basified with aqueous NaOH solution (2 M). The precipitate was collected by filtration and purified by column to afford (6-bromo-4-chloro-quinazolin-2-yl)-methyl-amine (5 g, 18.3 mmol, 46.6%) as a yellow solid. 1H NMR (DMSO-d6): δ 8.03 (s, 1H), 7.86-7.84 (m, 2H), 7.47-7.45 (d, 1H), 2.86-2.84 (d, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under N2 atmosphere for half an hour
  3. temperatureAfter cooling down
  4. filtrationThe precipitate was collected by filtration
  5. custompurified by column

Sources & evidence

ORD record
ord-ddb59a057d7a443dbf04b121b69d6a62
Source dataset
uspto-grants-2009_03
Patent number
US07501428B2

Reaction notes

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