Potassium Carbonate → HCID 57816881, compound

HRID 2197464Notes

Reaction equation

HRID 2197464 reaction equation
N[C:2]1([NH2:16])[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]1=[N:4][CH:5]=[N:6]2.C([O-])([O-])=O.[K+].[K+].[O:23]1[CH:25]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:24]1>CN(C=O)C>[NH2:16][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:24][CH:25]([OH:23])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31217Phenyl glycidyl etherHCID 68840948HCID 68840948, compound

Product 1

HCID 57816881HCID 57816881, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 6-amino-2-(2-methoxyethoxy)adenine (300 mg, 1.43 mmol) in DMF (3 ml) was added K2CO3 (200 mg, 1.43 mmol). Then 1,2-epoxy-3-phenoxy-propane (321 mg, 2.14 mmol) was added. The reaction mixture was stirred at 70° C. overnight. The solvent was removed and the residue was taken up in CH2Cl2 and washed with water. The aqueous phase was extracted with DCM. The organic layer was dried over NaSO4, filtered, concentrated, and purified by silica gel chromatography, using linear gradient of MeOH in DCM as eluent to give 350 mg product. 1H NMR (CDCl3): δ 3.43 (s, 3H), δ 3.74 (t, 2H), δ 3.90-4.06 (m, 2H), δ 4.30-4.35 (m, 1H), δ 4.30-4.50 (m, 4H), δ 6.00 (bs, 2H), δ 6.88-7.01 (m, 3H), δ 7.27-7.32 (m, 2H), δ 7.70-7.73 (m, 1H); MS: 360.2 (M+1).

Workup

  1. customThe solvent was removed
  2. washwashed with water
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-51ecb8775a354282b53f280a6818131d
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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