9-(Phenylmethyl)-9H-purin-6-amine → 9-Benzyl-8-bromoadenine

HRID 1297156

Reaction equation

HRID 1297156 reaction equation
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]([Br:18])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 202629-(Phenylmethyl)-9H-purin-6-amineHCID 67184N-bromobutanimide

Product 1

HCID 99045519-Benzyl-8-bromoadenine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 9-benzylpurine (6) (15.0 g, 66.5 mmol) in chloroform (750 mL) was added N-bromosuccinimide (59.26 g, 332.9 mmol) and the reaction mixture was stirred under an atmosphere of nitrogen at reflux temperature for 3 h. The reaction mixture was then transferred to a separatory funnel and washed with saturated aqueous sodium sulfite (2×250 mL) followed by brine solution (2×250 mL). The chloroform fraction was dried over anhydrous sodium sulfate and concentrated to give a reddish oil, which was purified by flash chromatography on silica gel using EtOAc/hexane (4:6) for elution. Yield 9.72 g. (48%). Mp 199-201° C. 1H NMR (CDCl3) δ 5.39 (s, 2H, benzylic CH2), 7.29-7.33 (m, 5H, Ar—H), 8.29 (s, 1H, purine C2—H).

Workup

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

Sources & evidence

ORD record
ord-a62ed5ace40c4759b36217e178163d4d
Source dataset
uspto-grants-2007_07
Patent number
US07250421B2

Linked notes

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