Tert-Butyl nitrite → 9-Benzyl-9H-purine

HRID 2099247Notes

Reaction equation

HRID 2099247 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]=2N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=O>C1COCC1.C(Cl)(Cl)Cl>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 202629-(Phenylmethyl)-9H-purin-6-amine

Product 1

HCID 2347019-Benzyl-9H-purine

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62.5 °C

Procedure

To a stirred suspension of 9-benzyladenine (6) (22.0 g, 97.6 mmol) in anhydrous THF (500 mL) was added t-butyl nitrite (9.34 g, 478.5 mmol) and the reaction mixture heated under an atmosphere of nitrogen at 60-65° C. for 4 h. THF and the excess reagent were distilled off and the residue obtained redissolved in chloroform (100 mL) and washed with brine solution (2×50 mL). The chloroform layer was dried over anhydrous sodium sulfate and distilled off to give a reddish oil, which was purified by flash chromatography on silica gel using EtOAc/hexane (8:2) for elution. Yield 10.68 g (42.3%). Mp 99-100° C. 1H NMR (CDCl3): δ 5.49 (s, 2H, CH2), 7.34-7.40 (m, 5H, Ar—H), 8.10 (s, 1H, purine C6—H), 9.06 (s, 1H, purine C8H), 9.20 (s, 1H, purine C2H).

Workup

  1. distillationTHF and the excess reagent were distilled off
  2. customthe residue obtained
  3. washwashed with brine solution (2×50 mL)
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. distillationdistilled off
  6. customto give a reddish oil, which
  7. customwas purified by flash chromatography on silica gel
  8. washfor elution

Sources & evidence

ORD record
ord-b1847d31a3704878b0d465b2faede328
Source dataset
uspto-grants-2009_08
Patent number
US07569573B2

Reaction notes

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