Kinetin → 6-Furfurylamino-9-(2-bromoethyl)purine

Reaction equation

[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[N:16]=[CH:15][N:14]=[C:10]3[N:11]=[CH:12][NH:13][C:9]=23)[O:4][CH:5]=1.C([O-])([O-])=O.[K+].[K+].[Br:23][CH2:24][CH2:25]Br>CN(C)C=O>[CH2:6]([NH:7][C:8]1[N:16]=[CH:15][N:14]=[C:10]2[C:9]=1[N:13]=[CH:12][N:11]2[CH2:25][CH2:24][Br:23])[C:3]1[O:4][CH:5]=[CH:1][CH:2]=1

Participants

Procedure

Kinetin (2 g, 9.3 mmol) and K2CO3 (2.4 g, 23 mmol) were mixed in 100 ml dimethylformamide (DMF). 1,2-Dibromoethane (5.2 g, 27.6 mmol) was added to the reaction mixture and then it was mixed at room temperature for 12 h, humidity was regulated by CaCl2 tube. Solvent was evaporated to dryness in vacuo to yellow solid and then 100 g ice was added. The mixture was shaken at least 1 h to until a white precipitate was formed. The solid was filtered off, washed with water and dried at 50° C. The product was recrystallised from methanol. Yield: 60%. 1H NMR (DMSO-d6): 3.95 (2H, t, J=5.91), 4.58 (2H, t, J=5.91), 4.69 (2H, s (br)), 6.23 (1H, d, J=2.94), 6.36 (1H, t, J=2.94), 7.54 (1H, d, J=2.94), 8.15 (2H, m), 8.24 (1H, s)