Reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:15][C:16]1[C:21]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:31].[CH3:32]OC(OC)OC>C1(C)C=CC=CC=1>[C:11]([C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:6])[N:31]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([B:22]4[O:26][C:25]([CH3:27])([CH3:28])[C:24]([CH3:30])([CH3:29])[O:23]4)[C:16]=3[CH3:15])[CH:32]=[N:1]2)=[CH:7][CH:8]=1)([CH3:14])([CH3:13])[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-Amino-4-tert-butyl-benzoic acid (78 mg, 0.41 mmol) in 2 mL trimethylorthoformate was heated to 105° C. for 30 minutes. The resulting solution was concentrated in vacuo. 2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (100 mg, 0.41 mmol) in 2 mL toluene was added. The resulting mixture was heated at reflux for 1 hour, concentrated in vacuo, and purified by flash chromatography (15% ethylacetate/hexanes) to yield 7-tert-Butyl-3-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3H-quinazolin-4-one (68 mg, 0.16 mmol). MS (ESI) 419.2 (M+H)+.
Workup
- concentrationThe resulting solution was concentrated in vacuo
- temperatureThe resulting mixture was heated
- temperatureat reflux for 1 hour
- concentrationconcentrated in vacuo
- custompurified by flash chromatography (15% ethylacetate/hexanes)
Sources & evidence
- ORD record
- ord-31175181f80a41b3b493d4b2dc90bcab
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822457B2
Linked notes
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