3-Bromoaniline → N-(3-Bromophenyl)-6-nitroquinazolin-4-amine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1>>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1Participants
Procedure
In one particular, 3-bromoaniline is reacted with 4-chloro-6-nitroquinazoline to produce 4-[(3-bromophenyl)amino]-6-nitro quinazoline, which is reduced thereafter, by means of an ethanolic solution of hydrazine hydrate and Raney®Nickel, to the corresponding 6-aminoquinazoline. The 4-[(3-bromophenyl)amino]-6-aminoquinazoline is then reacted with bistributyltin in the presence of tetrakis(triphenylphosphine)palladium in triethylamine solution and the obtained stanylated product is reacted thereafter with bromine-76, as described hereinabove. The obtained bromine-76 labeled 4-[(3-bromophenyl)amino]-6-aminoquinazoline is then reacted with an acryloyl chloride to produce a bromine-76 labeled {4-[(3-bromophenyl)amino]quinazoline-6-yl}acrylamide.
Sources & evidence
- ORD record
- ord-6806258138fb4f2ea611e84416c1ef35
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06562319B2
Reaction notes
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