3-(Trifluoromethyl)aniline → 6-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine

HRID 1668950Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([N+:24]([O-:26])=[O:25])[C:22]=1[CH3:23])[N:19]=[CH:18][N:17]=[C:16]2Cl>CC(O)C>[Br:12][C:13]1[CH:14]=[C:15]2[C:20](=[C:21]([N+:24]([O-:26])=[O:25])[C:22]=1[CH3:23])[N:19]=[CH:18][N:17]=[C:16]2[NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a microwave vial were added 3-(trifluoromethyl)aniline (343 μl, 2777 μmol), 6-bromo-4-chloro-7-methyl-8-nitroquinazoline (840 mg, 2777 μmol) and IPA (5 mL). The reaction mixture was heated to 140° C. for 20 min. On cooling a ppt was observed to form which was then washed with hexane, filtered and air-dried to afford 6-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine (569 mg, 48.0% yield) as an amorphous yellow solid. MS (M+H)+ 427, 429.

Workup

temperatureOn cooling a ppt
customto form which
washwas then washed with hexane
filtrationfiltered
customair-dried

Sources & evidence

ORD record: ord-72f93c4e0b0c4cd29bef5868eedf52ef
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989461B2

Reaction notes

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