p-Toluenesulfonic acid → 6-Chloro-9-isopropyl-9H-purine
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]([CH3:11])[CH3:10])[C:3]=1[NH2:12].[CH:13](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[N:12]=[CH:13][N:8]2[CH:9]([CH3:10])[CH3:11]Participants
4
Conditions
- Temperature
- 115 °C
Procedure
Compound 52A (268 mg, 1.44 mmol), triethyl orthoformate (2.4 ml, 14.36 mmol) and para-toluenesulfonic acid (27.3 mg, 0.144 mmol) were combined and heated at 115° C. overnight. Precipitation occurred upon cooling to room temperature. The precipitate was collected via filtration, rinsed with diethyl ether and dried under reduced pressure to yield the title compound 52B: 1H NMR (300 MHz, DMSO-d6) δ ppm 8.81 (1H, s), 8.78 (1H, s), 4.89 (1H, m), 1.58 (6H, d).