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 (comp. 52).
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