2-Aminopyrimidine → (2-Nitrophenyl)-pyrimidin-2-yl-amine

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]>CN(C=O)C>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([O-:19])=[O:18]

Participants

Procedure

To a solution of 2-aminopyrimidine (10 g, 105 mmol) in DMF (100 mL) cooled to 5° C. was added 60% sodium hydride in mineral oil (5.47 g, 137 mmol) and the resulting mixture was stirred one hour with cooling. 1-fluoro-2-nitrobenzene (14.83 g, 105 mmol) in DMF (30 mL) was added dropwise over a 20 minute period to the cooled, stirring solution. The solution was allowed to warm slowly to ambient temperature and stirred 3 h. The product was precipitated with the addition of water (300 mL), separated by filtration, and dried to give the title compound (13.39 g, 61.9 mmol) as an orange solid: 1H NMR (Acetone-d6, 400 MHz): 10.34 (br s, 1H), 9.00 (d, 1H, J=8.6 Hz), 8.60 (d, 2H, J=4.8 Hz), 8.23 (d, 1H, J=8.4 Hz), 7.74 (t, 1H), 7.17 (t, 1H), 7.06 (t, 1H); TLC (EtOAc/Hexanes (3:17)): Rf =0.27.