6-Amino-9-benzyl-8-bromo-2-(3-hydroxypropoxy)purine → 6-Amino-9-benzyl-2-(3-hydroxypropoxy)-8-methoxypurine
Reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][OH:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:24][O-:25].[Na+].CO>CO>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][OH:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:25][CH3:24])[N:6]2[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-Amino-9-benzyl-8-bromo-2-(3-hydroxypropoxy)purine (140 mg, 0.37 mmol) in methanol (50 ml) was dissolved in 28%. sodium methoxide/methanol (3 ml) and the solution was refluxed on heating under stirring for 10 hours. The reaction mixture was concentrated in vacuo to dryness and to the residue was added saturated brine. The mixture was extracted with chloroform and the organic layer was dried on sodium sulfate and the solvent was removed. The residue was purified with silica gel chromatography (3% methanol/chloroform) to give the subject compound (88 mg, yield 72%).