Phenacyl bromide → HCID 57816849, compound

HRID 2197466Notes

Reaction equation

HRID 2197466 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+].Br[CH2:24][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26]>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][C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 68840948HCID 68840948, compound

Product 1

HCID 57816849HCID 57816849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 6-amino-2-(2-methoxyethoxy)adenine (500 mg, 2.39 mmol) in DMF (5 ml) was added K2CO3 (330 mg, 2.39 mmol). Then 2-bromoacetophenone was added and the reaction mixture was heated to 70° C. with stirring for 30 min. The solvent was removed under vacuum and the residue was washed with brine. The aqueous phase was extracted with DCM and the organic layer was dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography using linear gradient of MeOH in DCM as eluent. 1H NMR (CDCl3) δ 3.40 (s, 3H), δ 3.72 (t, 2H), δ 4.45 (t, 2H), δ 5.58 (s, 2H), δ 5.67 (bs, 2H), δ 7.53-7.74 (m, 4H), δ 8.03 (s, 1H), δ 8.06 (s, 1H); MS: 328.2 (M+1), 326.0 (M−1).

Workup

  1. customThe solvent was removed under vacuum
  2. washthe residue was washed with brine
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-171f53e468c64babad588890f43fd52b
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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