Isopropylamine → 6-Chloro-N4-isopropylpyrimidine-4,5-diamine
Reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[CH3:10][CH:11]([NH2:13])[CH3:12].CCN(CC)CC>>[Cl:9][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:13][CH:11]([CH3:12])[CH3:10])[C:7]=1[NH2:8]Participants
4
Procedure
4,6-Dichloropyrimidin-5-amine (492 mg, 3 mmol), propan-2-amine (284 μl, 3.3 mmol) and Et3N (836 μl, 6 mmol) were combined and heated at reflux. The mixture was refluxed for 5 days and each day additional isopropylamine (0.77 mL, 9 mmol) was added. The reaction mixture was cooled to room temperature, concentrated, slurried in water, filtered, rinsed with additional water and dried under reduced pressure to provide the title compound 52A as a tan solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.72 (1H, s), 6.53 (1H, d), 5.02 (2H, s), 4.20 (1H, octet), 1.18 (6H, d).