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

HRID 400332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400332
[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

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 8536776-Benzyloxypurine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 22056973Butanol acetic acid waterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d9b33f15ebec4ecd96476e366eafab89
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741566B2

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