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

HRID 1297153

반응식

HRID 1297153 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

HCID 2347019-Benzyl-9H-purine

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
62.5 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-260b257c25d94c08a3539aa93c66f71e
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250421B2

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