CC1C=CC=CC=1B(O)O.N[C:12]1[N:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([O:29][CH3:30])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:18]=2)[N:13]=1.[I:31]I.[I-].[Cs+].N(OCCC(C)C)=O>COCCOC.[Cu](I)I>[I:31][C:12]1[N:21]=[CH:20][C:19]2[C:14](=[CH:15][C:16]([O:29][CH3:30])=[C:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[CH:18]=2)[N:13]=1
In a similar manner to Example 4, 2-amino-7-methoxy-6-(2-methylphenyl)quinazoline was obtained using Compound A2 and 2-methylphenylboronic acid. The obtained 2-amino-7-methoxy-6-(2-methylphenyl)quinazoline (4.38 g, 16.5 mmol) was dissolved in DME (165 mL) and the solution was added with iodine (1.05 g, 8.3 mmol), cesium iodide (4.3 g, 16.5 mmol), isoamyl nitrite (13.3 mL, 99 mmol) and copper iodide (3.1 g, 16.5 mmol), followed by stirring at 80° C. for 7 hours. After an insoluble matter was filtered off from the reaction mixture, the solvent was evaporated under reduced pressure. The residue was added with aqueous saturated sodium thiosulfate solution and 28% aqueous ammonia and the obtained crystal was collected by filtration to obtain 2-iodo-7-methoxy-6-(2-methylphenyl)quinazoline (5.76 g, 93%) as a crude product. In a similar manner to Reference Example 4 and Example 19, Compound 174 was obtained using the above-obtained 2-iodo-7-methoxy-6-(2-methylphenyl)quinazoline and 4-heptylamine.
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