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

HRID 271269

Reaction equation

HRID 271269 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 59834959Methyl 3-(2-amino-6-(2-furyl)-9H-purine-9-yl)propionateYield 11.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)]

Sources & evidence

ORD record
ord-3c35fbd01a794b259e7c22e35a4be0c5
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Linked notes

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