2-Pentanol → 2-[(1-Methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine
Reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH2:17])[N:3]=1.[CH3:18][CH:19]([OH:23])[CH2:20][CH2:21][CH3:22].[H-].[Na+]>>[CH3:18][CH:19]([O:23][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([NH2:17])[N:3]=1)[CH2:20][CH2:21][CH3:22]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
In a separate flask, a suspension of 2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (500 mg) and 2-pentanol (3.8 mL) was heated to 50° C. Sodium hydride (396 mg, 60% dispersion) was added in portions and the reaction was stirred at 50° C. for 72 h. The reaction was cooled and quenched with water (10 mL) and was extracted with EtOAc (3×25 mL). The combined organics were washed with brine (30 mL), dried over MgSO4, filtered and concentrated in vacuo to give crude title compound as a yellow oil.