1-Butanol → 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-6-phenyl-7H-purin-8(9H)-one
Reaction equation
Cl[C:2]1[N:10]=[C:9]([N:11]2[C:15]3[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=3[N:13]=[CH:12]2)[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:32])[N:6]2[C@H:21]1[C:30]2[C:25](=[C:26]([F:31])[CH:27]=[CH:28][CH:29]=2)[O:24][CH2:23][CH2:22]1.[CH2:33](O)[CH2:34][CH2:35][CH3:36].[C:38](#N)[CH3:39]>>[F:20][C:17]1[CH:18]=[CH:19][C:14]2[N:13]=[CH:12][N:11]([C:9]3[N:8]=[C:7]4[C:3]([NH:4][C:5](=[O:32])[N:6]4[C@H:21]4[C:30]5[C:25](=[C:26]([F:31])[CH:27]=[CH:28][CH:29]=5)[O:24][CH2:23][CH2:22]4)=[C:2]([C:33]4[CH:39]=[CH:38][CH:36]=[CH:35][CH:34]=4)[N:10]=3)[C:15]=2[CH:16]=1Participants
4
Conditions
- Temperature
- 110 °C
Procedure
General procedure for displacement reactions of 6-chloropurinones with aliphatic amines. To 10 mg (0.022 mmol) of 6-chloro-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-9-((R)-8-fluorochroman-4-yl)-7H-purin-8(9H)-one was added 0.6 mL of 1-butanol, followed by an aliphatic amine (0.1 mL), and the reaction mixture was stirred at 110° C. for 1-2 h (HPLC monitoring). Upon completion of the reaction, the mixture was left to cool to room temperature, was diluted with acetonitrile and filtered through a Nylon 0.45 μm filter. Preparative HPLC purification afforded, after solvent evaporation and drying, the desired product.