Sodium Iodide → 5-Iodopyrazolo[1,5-A]pyrimidine

HRID 751280노트

반응식

HRID 751280 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1.[I-:11].[Na+].C(Cl)(=O)C.C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])=O.[Na+].[Na+]>C(#N)C.C(OCC)C>[I:11][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][CH:10]=[C:4]2[N:3]=1

참가 물질

8

반응물 5

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 210717595-Chloropyrazolo(1,5-a)pyrimidine

생성물 1

HCID 497615315-Iodopyrazolo[1,5-A]pyrimidine수율 51.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

실험 절차

Dissolve 5-chloro-pyrazolo[1,5-a]pyrimidine (Hans Reimlinger et al., Chem. Ber. 1970, 103, 3252-3265; 1.15 g, 7.5 mmol) and sodium iodide (5.6-g, 37.4 mmol) in anhydrous acetonitrile (50 mL). Add acetyl chloride (2.7 ml, 37.9 mmol). Stir and reflux under nitrogen for 20 h. Pour the reaction mixture into a stirring mixture of 0.5M aqueous potassium carbonate (200 mL), 1.0M aqueous sodium sulfite (50 mL), and diethyl ether (350 mL). Separate the organic layer, dry over anhydrous magnesium sulfate, filter and concentrate under reduced pressure. Chromatograph the crude product on flash silica using neat dichloromethane to obtain 950 mg (51%) of the title compound as a yellow solid. TOF MS ES+ exact mass calculated for C6H4N310): m/z=245.9528; Found: 245.9517. 1H NMR (400 MHz, DMSO-d6) δ 8.82 (d, J=7 Hz, 1H), 8.18 (d, J=2 Hz, 1H), 7.32 (d, J=7 Hz, 1H), 6.69 (d, J=2 Hz, 1H).

후처리

  1. temperaturereflux under nitrogen for 20 h
  2. additionPour the reaction mixture
  3. customSeparate the organic layer
  4. dry with materialdry over anhydrous magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-7d5e51ceb5694f19a478045568068a57
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405299B2

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