4-Fluoro-N-methylaniline → N-(4-Fluorophenyl)-N,2-dimethylquinazolin-4-amine

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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[CH:16][CH:15]=1>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[N:3]=2)[CH3:21])=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 680244-Fluoro-N-methylaniline

HCID 27854214-Chloro-2-methylquinazoline

Product 1

HCID 11311671N-(4-Fluorophenyl)-N,2-dimethylquinazolin-4-amine

Procedure

The title compound was prepared from 4-chloro-2-methyl-quinazoline (178.6 mg, 1.0 mmol) and (4-fluoro-phenyl)-methyl-amine (125 mg, 2.52 mmol) by a procedure similar to Example 28 (46.8%). 1H NMR (CDCl3): 7.76 (dd, J=0.9 Hz, J=8.3 Hz, 1H), 7.58-7.52 (m,1H), 7.16-7.00 (m, 6H), 3.60 (s, 3H), 2.73 (s, 3H),

Sources & evidence

ORD record: ord-52875d1462464706a2a1b965fe32fc48
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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