Potassium Carbonate → Methyl [6-(benzyloxy)-9H-purin-9-yl]acetate

HRID 1473751Notes

Reaction equation

HRID 1473751 reaction equation
[CH2:1]([O:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[NH:11][CH:12]=[N:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:24][O:25][C:26](=[O:29])[CH2:27]Br>CN(C=O)C.C(O)CCC.C(O)(=O)C.O>[CH2:1]([O:8][C:9]1[N:17]=[CH:16][N:15]=[C:14]2[C:10]=1[N:11]=[CH:12][N:13]2[CH2:27][C:26]([O:25][CH3:24])=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 8536776-Benzyloxypurine

Product 1

HCID 59289995Methyl [6-(benzyloxy)-9H-purin-9-yl]acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22056973Butanol acetic acid waterSolvent

Procedure

6-Benzyloxypurine (4.18 g; 18.5 mmol) was added to a suspension of potassium carbonate (3.1 g; 22.4 mmol) in DMF (100 ml). After 15 min., bromoacetic acid methyl ester (1.93 ml; 20.4 mmol) was added. The reaction was monitored by TLC in butanol:acetic acid:water 4:1:1. Upon completion, the reaction mixture was partitioned between water (600 ml) and ethyl acetate (600 ml). The organic phase was dried over magnesium sulfate and evaporated to a volume of −10 ml and precipitated with pet. ether. The two products were separated by column chromatography using ethyl acetate as the solvent. The products were precipitated in pet. ether. Yield: 2.36 g (43%). Melting point: 111.5-115° C. UV λmax=250 nm (9-alkylated); λmax=260 nm (7-alkylated). 1H-NMR (DMSO-d6): 8.60 (1H, s); 8.43 (1H, s); 7.6-7.35 (5H, m); 5.69 (2H, s); 5.26 (2H, s); 3.75 (3H, s).

Workup

  1. customUpon completion, the reaction mixture was partitioned between water (600 ml) and ethyl acetate (600 ml)
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated to a volume of −10 ml
  4. customprecipitated with pet. ether
  5. customThe two products were separated by column chromatography
  6. customThe products were precipitated in pet. ether

Sources & evidence

ORD record
ord-1f2c22ff7af74f62b99d034bc6ba435d
Source dataset
uspto-grants-2015_04
Patent number
US09017992B2

Reaction notes

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