N-bromobutanimide → 8-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011024Notes

Reaction equation

HRID 1011024 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[C:8]([NH2:21])[N:7]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:22][C:11]1[N:12]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:13]2[C:9]([N:10]=1)=[C:8]([NH2:21])[N:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:14]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57699621[2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576997398-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amineYield 70.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

2-{[2-(Methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.61 g) was dissolved in chloroform (20 mL) and cooled to 0° C. To this solution was then added N-bromosuccinimide (1.02 g) gradually, keeping the temperature at ˜2° C. The reaction was stirred at 2° C. for around 15 minutes before being allowed to warm to room temperature. The reaction mixture was then stirred under nitrogen for 5 hours. The reaction mixture was quenched with water (100 mL) and stirred rapidly before the organic layer was separated using a hydrophobic frit. The organic was evaporated under reduced pressure to give a dark brown gum. This material was purified by silica chromatography (ISCO) eluting initially with 0-70% ethyl acetate: cyclohexane holding isocratic at 70% ethyl acetate; cyclohexane until a minor impurity was eluted. The gradient was then resumed from 70%-95% ethyl acetate: cyclohexane. This gave the title compound as a white solid (1.4489 g)

Workup

  1. customat ˜2° C
  2. temperatureto warm to room temperature
  3. stirringThe reaction mixture was then stirred under nitrogen for 5 hours
  4. customThe reaction mixture was quenched with water (100 mL)
  5. stirringstirred rapidly before the organic layer
  6. customwas separated
  7. customThe organic was evaporated under reduced pressure
  8. customto give a dark brown gum
  9. customThis material was purified by silica chromatography (ISCO)
  10. washeluting initially with 0-70% ethyl acetate
  11. washcyclohexane until a minor impurity was eluted

Sources & evidence

ORD record
ord-8614b8e95dbb4d0894a89e294f1ca779
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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