3,4,5-Trimethoxyaniline → 2-Methyl-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine

HRID 1668803Notes

Reaction equation

HRID 1668803 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[NH2:18].C([O-])(=O)C.[Na+]>>[CH3:12][C:4]1[N:3]=[C:2]([NH:18][C:17]2[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:15]([O:14][CH3:13])[CH:16]=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 3

HCID 322853,4,5-TrimethoxyanilineHCID 517045Sodium AcetateHCID 27854214-Chloro-2-methylquinazoline

Product 1

HCID 596483692-Methyl-N-(3,4,5-trimethoxyphenyl)quinazolin-4-amine

Procedure

The title compound was prepared from 4-chloro-2-methyl-quinazoline (179 mg, 1.0 mmol), 3,4,5-trimethoxy-aniline (183 mg, 1.0 mmol) and sodium acetate (98.4 mg, 1.2 mmol) similar to example 20 to give 239 mg (73.5%) of white solids. 1H NMR (CDCl3): 7.88 (t, J=7.2 Hz, 2H), 7.77 (t, J=7.2 Hz, 1H), 7.51 (t, J=8.1 Hz, 2H), 7.22 (s, 2H), 3.92-3.87 (m, 9H), 2.72 (s, 3H).

Sources & evidence

ORD record
ord-77c7208349dd4f65be59356fee68d0b0
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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