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

HRID 2099247ノート

反応式

HRID 2099247 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 2347019-Benzyl-9H-purine

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
62.5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b1847d31a3704878b0d465b2faede328
出典データセット
uspto-grants-2009_08
特許番号
US07569573B2

反応ノート

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