N-bromobutanimide → HCID 57579036, compound

HRID 881799Notes

Reaction equation

HRID 881799 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]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21].BrN1[C:30](=[O:31])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]([O:31][CH3:30])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57579059HCID 57579059, compound

Product 1

HCID 57579036HCID 57579036, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-((6-amino-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzonitrile (7) (1.0 g) was suspended in acetonitrile. N-Bromosuccinimide (1.0 g) was added in small portions over 10 minutes. After stirring for 1 hour, the mixture was diluted with ethyl acetate, washed with 10% aqueous Na2S2O3 solution, saturated aqueous NaHCO3 solution and brine, dried with Na2SO4 and evaporated to dryness under vacuum. The crude 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzonitrile (8) was dissolved in methanol (50 mL) and 50% aqueous KOH solution (1 mL) was added. The mixture was heated under reflux for 3 hours and then concentrated under vacuum. The product was extracted with ethyl acetate, the combined organic layers were washed with water and brine, dried with Na2SO4 and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: 0-10% MeOH in ethyl acetate) gave 3-((6-amino-8-methoxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzonitrile (9) (0.45 g) as a pinkish solid.

Workup

  1. washwashed with 10% aqueous Na2S2O3 solution, saturated aqueous NaHCO3 solution and brine
  2. dry with materialdried with Na2SO4
  3. customevaporated to dryness under vacuum
  4. dissolutionThe crude 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)benzonitrile (8) was dissolved in methanol (50 mL)
  5. addition50% aqueous KOH solution (1 mL) was added
  6. temperatureThe mixture was heated
  7. temperatureunder reflux for 3 hours
  8. concentrationconcentrated under vacuum
  9. extractionThe product was extracted with ethyl acetate
  10. washthe combined organic layers were washed with water and brine
  11. dry with materialdried with Na2SO4
  12. customevaporated under vacuum
  13. customPurification by flash chromatography on silica gel (eluent: 0-10% MeOH in ethyl acetate)

Sources & evidence

ORD record
ord-126ddb7a622a4c6fa395688ef25dfa25
Source dataset
uspto-grants-2015_03
Patent number
US08993755B2

Reaction notes

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