Ammonium formate → 7-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine

HRID 1668951Notes

Reaction equation

C([O-])=O.[NH4+].Br[C:6]1[CH:7]=[C:8]2[C:13](=[C:14]([N+:17]([O-])=O)[C:15]=1[CH3:16])[N:12]=[CH:11][N:10]=[C:9]2[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1>C(O)C.[Pd]>[CH3:16][C:15]1[C:14]([NH2:17])=[C:13]2[C:8]([C:9]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:28])[F:29])[CH:22]=3)=[N:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a microwave vial were added ammonium formate (131 μl, 2664 μmol), 6-bromo-7-methyl-8-nitro-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine (569 mg, 1332 μmol), and palladium black (11.8 μl, 1332 μmol) in ethanol (10 mL). The reaction mixture was heated to 140° C. for 20 min under microwave conditions and taking care to monitor the pressure in the reaction vessel. On cooling the reaction mixture was filtered through celite and filtrate concentrated in vacuo to afford 7-methyl-N4-(3-(trifluoromethyl)phenyl)quinazoline-4,8-diamine (238 mg, 56.1% yield). MS (M+H)+ 319.

Workup

temperatureOn cooling the reaction mixture
filtrationwas filtered through celite and filtrate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-059ca40293fa4bc987c316afc264965d
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989461B2

Reaction notes

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