Methanol → 6-Amino-9-benzyl-2-(4-hydroxybutoxy)-8-methoxypurine

Reaction equation

[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-:25].[Na+].[CH3:27]O>>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:27])[N:6]2[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Reactant 3

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 18332702HCID 18332702, compound

Product 1

HCID 183327246-Amino-9-benzyl-2-(4-hydroxybutoxy)-8-methoxypurineYield 68%

Procedure

To 6-amino-9-benzyl-8-bromo-2-(4-hydroxybutoxy)purine (185 mg, 0.472 mmol) in 10 ml of methanol was added 1N aqueous sodium hydroxide (40 ml). The mixture was refluxed on heating under stirring for 2 hours. The reaction mixture was concentrated in vacuo to dryness. To the residue was added water and the mixture was extracted with chloroform. The organic layer was dried on sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography (2% methanol/chloroform) to give the subject compound (123 mg, yield 68%).