Methyl Acrylate → Methyl 3-(2-amino-6-(2-furyl)-9H-purine-9-yl)propionate

HRID 271269

Reaktionsgleichung

Reaktionsgleichung von HRID 271269
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:14][C:13]([NH2:15])=[N:12][C:11]2[C:7]=1[N:8]=[CH:9][N:10]=2.C([O-])([O-])=O.[K+].[K+].[C:22]([O:26][CH3:27])(=[O:25])[CH:23]=[CH2:24]>CN(C=O)C.CCOC(C)=O>[NH2:15][C:13]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[CH2:24][CH2:23][C:22]([O:26][CH3:27])=[O:25])=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:14]=1

Komponenten

6

Edukt 3

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

Produkt 1

HCID 59834959Methyl 3-(2-amino-6-(2-furyl)-9H-purine-9-yl)propionateAusbeute 11,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 6-(2-furyl)-1H-purine-2-amine (0.70 g, 3.48 mmol) and K2CO3 (0.48 g, 3.48 mmol) in DMF (20 mL) was treated with methyl acrylate (3.3 g, 38.3 mmol), stirred for 40 h, diluted with EtOAc, filtered to remove polymeric acrylate, washed with water, dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2: EtOAc-heptane, (4:1)] to give the title compound (114 mg, 11%) as a white solid.

Aufarbeitung

  1. filtrationfiltered
  2. customto remove polymeric acrylate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography [SiO2: EtOAc-heptane, (4:1)]

Quellen und Nachweise

ORD-Eintrag
ord-3c35fbd01a794b259e7c22e35a4be0c5
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452894B2

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