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

HRID 751280ノート

反応式

HRID 751280 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7d5e51ceb5694f19a478045568068a57
出典データセット
uspto-grants-2008_07
特許番号
US07405299B2

反応ノート

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