Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[N:3]=1.[NH2:18][C:19]1[C:26]([CH3:27])=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=1[CH3:28].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>C(Cl)Cl.O1CCOCC1.CN1CCCC1=O>[C:14]([C:13]1[CH:16]=[CH:17][C:10]([NH:9][C:4]2[N:3]=[C:2]([NH:18][C:19]3[C:20]([CH3:28])=[CH:21][C:22]([C:23]#[N:24])=[CH:25][C:26]=3[CH3:27])[C:7]([CH3:8])=[CH:6][N:5]=2)=[CH:11][CH:12]=1)#[N:15]
4-[[4-[(4-chloro-5-methyl-2-pyrimidinyl]amino]benzonitrile (0.01541 mol), 4-amino-3,5-dimethyl-benzonitrile (0.00219 mol), 1-methyl-2-pyrrolidinone (4 ml), 1,4-dioxane (15 ml) and diisopropylethylamine (0.0154 mol) were combined in a flask under a stream of argon and heated at 160-230° C. for 16 hours. CH2Cl2 and 1N NaOH were added, and the mixture was stirred 1 hour and filtered to give a brown solid (*). The CH2Cl2 filtrate was separated and was evaporated and purified by flash column chromatography (eluent: 2% CH3OH/CH2Cl2). The desired fractions were combined, evaporated and the residue was stirred in CH2Cl2. The solid precipitate was filtered off, combined with the brown solid (*) and recrystallized from CH3CN. The precipitate was filtered off and dried, yielding 1.57 g (29%) of 4-[[2-[(4-cyanophenyl)amino]-5-methyl-4-pyrimidinyl]amino]-3,5-dimethylbenzonitrile (compound 89).
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