N-bromobutanimide → HCID 58054330, compound

HRID 2066410Notes

Reaction equation

HRID 2066410 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1.[Br:18]N1C(=O)CCC1=O>C(#N)C>[Br:18][C:7]1[N:8]([CH3:11])[C:9]2[C:5]([N:6]=1)=[C:4]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[N:3]=[C:2]([Cl:1])[N:10]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 715006872-Chloro-9-methyl-6-(4-morpholinyl)-9H-purine

Product 1

HCID 58054330HCID 58054330, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4-(2-chloro-9-methyl-9H-purin-6-yl)morpholine (5.08 g, 20.0 mmol) in acetonitrile (100 mL) was added N-bromosuccinimide (5.34 g, 30.0 mmol). The mixture was heated at 60° C. for 4 h. Cooled to rt, the contents were concentrated on a rotary evaporator. The remaining slurry was diluted with DCM and washed with a mixture of diluted Na2CO3 and NaHSO3 (2×), dried (Na2SO4), filtered and concentrated. The slightly orange solid was triturated with hot acetonitrile (˜70 mL). After cooled to room temperature (rt), the solid was collected with filtration and washed with acetonitrile. The filtrate was concentrated (to ˜30 mL) to yield a second crop. The product was dried in air then under vacuum to give 4-(8-bromo-2-chloro-9-methyl-9H-purin-6-yl)morpholine (5.67 g, 85%). LCMS: M+H+=332.0, 334.0.

Workup

  1. temperatureCooled to rt
  2. concentrationthe contents were concentrated on a rotary evaporator
  3. additionThe remaining slurry was diluted with DCM
  4. washwashed with a mixture of diluted Na2CO3 and NaHSO3 (2×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe slightly orange solid was triturated with hot acetonitrile (˜70 mL)
  9. temperatureAfter cooled to room temperature (rt)
  10. filtrationthe solid was collected with filtration
  11. washwashed with acetonitrile
  12. concentrationThe filtrate was concentrated (to ˜30 mL)
  13. customto yield a second crop
  14. customThe product was dried in air

Sources & evidence

ORD record
ord-1a279d54ff964a589847e90bd551c7ff
Source dataset
uspto-grants-2012_10
Patent number
US08293736B2

Reaction notes

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