Methyl iodide → (3,4-Dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-methylamine

HRID 1668801Notes

Reaction equation

HRID 1668801 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]=[C:14]([CH3:25])[N:13]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:26]I.[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-:24])=[O:23])[CH:20]=3)[N:15]=[C:14]([CH3:25])[N:13]=2)[CH3:26])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59648372(3,4-Dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-amine

Product 1

HCID 11653274(3,4-Dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-methylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from (3,4-dimethoxy-phenyl)-(2-methyl-6-nitro-quinazolin-4-yl)-amine (105 mg, 0.31 mmol), methyl iodide (0.029 ml, 0.46 mmol), sodium hydride (19 mg, 0.46 mmol, 60% oil dispersion) in DMF similar to example 21 to give 10.1 mg (9.2%) of yellow solids. 1H NMR (CDCl3): 8.30-8.62 (m, 1H), 7.91 (d, J=2.4 Hz, 1H), 7.76 (d, J=9.3 Hz, 1H), 6.97 (d, J=8.4 Hz, 1H), 6.86-6.82 (m, 1H), 6.74 (d, J=2.7 Hz, 1H), 3.95 (s, 3H)), 3.81 (s, 3H), 3.66 (s, 3H), 2.73 (s, 3H).

Sources & evidence

ORD record
ord-8e6f5a6229dc4a8fb10b44dae0f8b366
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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