Potassium Carbonate → HCID 57816876, compound

HRID 2197468Notes

Reaction equation

HRID 2197468 reaction equation
[O:1]([CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([NH2:15])[N:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C=O)C>[CH2:27]([O:26][C:24](=[O:25])[CH:23]([N:12]1[CH:11]=[N:10][C:9]2[C:13]1=[N:14][C:6]([O:5][CH2:4][CH2:3][O:1][CH3:2])=[N:7][C:8]=2[NH2:15])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 97780Ethyl bromophenylacetateHCID 23079491HCID 23079491, compound

Product 1

HCID 57816876HCID 57816876, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-methoxylethoxyadenine (500 mg, 2.39 mmol) in DMF (5 ml), was added K2CO3 (329 mg, 2.39 mmol) and ethyl α-bromophenylacetate (460 μl, 2.68 mmol). The reaction mixture was allowed to react at 70° C. for 2 h. The reaction mixture was washed with water and extracted by DCM. The organic later was dried over Na2SO4. The organic layer then was filtered, concentrated and purified by silica gel column, using dichlormethane and MeOH as the solvent in a linear gradient. 1H NMR (CDCl3): δ 1.31 (t, 3H), δ 3.45 (s, 3H), δ 3.78 (t, 2H), δ 4.29-4.33 (m, 2H), δ 4.51 (t, 2H), δ 5.83 (bs, 2H), δ 7.41-7.42 (m, 5H), δ 7.78 (s, 1H); MS: 372.1 (M+H)+, 370.1 (M−1).

Workup

  1. customto react at 70° C. for 2 h
  2. washThe reaction mixture was washed with water
  3. extractionextracted by DCM
  4. dry with materialThe organic later was dried over Na2SO4
  5. filtrationThe organic layer then was filtered
  6. concentrationconcentrated
  7. custompurified by silica gel column

Sources & evidence

ORD record
ord-abde2eaf2df449d9945a161719e9bae8
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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