[CH3:1][NH:2][C:3]1[N:8]=CC=C[N:4]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.O.NN.O>C(#N)C>[CH3:1][N:2]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][N:4]=[C:3]1[NH2:8]To a microwave vial containing a solution of N-methylpyrimidin-2-amine (90b, 290 mg, 2.7 mmol) in acetonitrile (5 mL) was added 2-bromo-1-phenylethanone (714 mg, 3.6 mmol). The vial was sealed and heated in a microwave reactor at 130° C. for 20 minutes and then cooled to room temperature. The reaction mixture was treated with hydrazine hydrate (0.65 mL, 13.3 mmol) and then heated in a microwave reactor at 100° C. for 5.0 minutes. The solution was poured into water and filtered the precipitate to give 1-methyl-5-phenyl-1H-imidazol-2-ylamine (90c).
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