[CH3:1][N:2](C)C.Cl[C:6]1[N:11]=[C:10]([O:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([NH2:23])=[CH:15][CH:14]=2)[CH:9]=[CH:8][N:7]=1>CN(C)C=O.[C-]#N.C([N+](CC)(CC)CC)C>[NH2:23][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]([O:12][C:10]2[CH:9]=[CH:8][N:7]=[C:6]([C:1]#[N:2])[N:11]=2)=[CH:14][CH:15]=1To a 0° C. solution of trimethyl amine (20% solution in water, 3.8 mmol) in 2 mL of dimethylformamide was added 4-(2-chloro-pyrimidin-4-yloxy)-naphthalen-1-ylamine (270 mg, 1 mmol). The deep tan solution was warmed to room temperature for 3 h, during which the initially light suspension became a brown suspension. After this time, tetraethylammonium cyanide (156 mg, 1 mmol) was added all at once to provide a deep amber solution. After 1 h, the reaction was quenched with water, extracted with EtOAc and dried over magnesium sulfate. Column chromatography (10-60% EtOAc-hexanes) provided 142 mg (54%) of 4-(4-amino-naphthalen-1-yloxy)-pyrimidine-2-carbonitrile.
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