9-Benzyl-9H-purine → 9-Benzyl-8-bromo-9H-purine

HRID 2099248Notes

Reaction equation

HRID 2099248 reaction equation
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]NC(=O)CCC(N)=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]([Br:17])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2347019-Benzyl-9H-purineHCID 9834204N-Bromosuccinamide

Product 1

HCID 589145899-Benzyl-8-bromo-9H-purine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 12 (10.68 g, 50.7 mmol) in chloroform (500 mL) was added N-bromosuccinamide (45.20 g, 253.9 mmol) and the reaction mixture stirred under an atmosphere of nitrogen and at reflux temperature for 5 h. The reaction mixture was transferred to a separatory funnel and washed with saturated sodium sulfite solution (2×250 mL) followed by brine solution (2×250 mL). The chloroform fraction was dried over anhydrous sodium sulfate and concentrated and the reddish oil was purified by flash chromatography on silica gel using EtOAc/hexane (4:6) for elution. Yield 6.05 g. (41.2%). Mp 119-121° C.; 1H NMR (CDCl3): δ 5.53 (s, 2H, CH2), 7.35-7.39 (m, 5H, Ar—H), 9.03 (s, 1H, purine C8—H), 9.09 (s, 1H, purine C2—H).

Workup

  1. temperatureat reflux temperature for 5 h
  2. customThe reaction mixture was transferred to a separatory funnel
  3. washwashed with saturated sodium sulfite solution (2×250 mL)
  4. dry with materialThe chloroform fraction was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe reddish oil was purified by flash chromatography on silica gel
  7. washfor elution

Sources & evidence

ORD record
ord-58e46a8af38e4ce18f2f04f65d5cc752
Source dataset
uspto-grants-2009_08
Patent number
US07569573B2

Reaction notes

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