6-Amino-9-benzyl-8-bromo-2-(3-hydroxypropoxy)purine → 6-Amino-9-benzyl-2-(3-hydroxypropoxy)-8-methoxypurine

HRID 2269162Notes

Reaction equation

HRID 2269162 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]=1

Participants

4

Reactant 2

HCID 183327536-Amino-9-benzyl-8-bromo-2-(3-hydroxypropoxy)purineHCID 23694274Sodium methanolate methanol

Product 1

HCID 183327906-Amino-9-benzyl-2-(3-hydroxypropoxy)-8-methoxypurineYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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%).

Workup

  1. temperatureon heating
  2. concentrationThe reaction mixture was concentrated in vacuo to dryness and to the residue
  3. additionwas added saturated brine
  4. extractionThe mixture was extracted with chloroform
  5. customthe organic layer was dried on sodium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified with silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-65fc4c3eb8df44b49cf1d55feda17ec0
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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