N-bromobutanimide → HCID 86617440, compound

HRID 2197461Notes

Reaction equation

HRID 2197461 reaction equation
[NH2:1][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[CH2:16][C:17]1[CH:18]=[C:19]([P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[CH:20]=[CH:21][CH:22]=1.[Br:31]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[NH2:1][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]=[C:5]([Br:31])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57816841HCID 57816841, compound

Product 1

HCID 86617440HCID 86617440, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl 3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (30) (400 mg, 0.92 mmol) was dissolved in acetonitrile and N-bromosuccinimide (500 mg, 2.8 mmol) was added in one portion. After stirring at room temperature for 2 h, the reaction mixture was diluted with ethyl acetate (150 mL) and washed with water, 0.2 M sodium thiosulfate solution and brine. The organic phase was dried with sodium sulfate and the solvent was removed under vacuum. The crude diethyl 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (450 mg, 95%) was used in the next step without further purification.

Workup

  1. washwashed with water, 0.2 M sodium thiosulfate solution and brine
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. customthe solvent was removed under vacuum
  4. customThe crude diethyl 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (450 mg, 95%) was used in the next step without further purification

Sources & evidence

ORD record
ord-0e5c9db5468346d782193693a97b9749
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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