Potassium Iodide → 2-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyrimidin-4-amine

HRID 875196노트

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HRID 875196 반응식
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[N:9][OH:10])[S:4][N:3]=1.Cl[CH2:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=1.[I-].[K+].N12CCCC1=NCCC2>C(#N)C>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](=[N:9][O:10][CH2:17][C:18]2[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=2)[C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[S:4][N:3]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 212988272-(Chloromethyl)pyrimidin-4-amineHCID 1363312531-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine

생성물 1

HCID 866507352-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyrimidin-4-amine수율 6.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

To a stirred suspension of 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine (1.69 g, 6.06 mmol), 2-(chloromethyl)pyrimidin-4-amine (957 mg, 6.66 mmol) and potassium iodide (1.01 g, 6.06 mmol) in acetonitrile (15 mL) at 0° C. was added 1,5-diazabicyclo(4.3.0)non-5-ene (1.52 mL, 12.7 mmol). The mixture was stirred 10 min at 0° C., then overnight at room temperature. After dilution of the reaction mixture with water and extraction with ethyl acetate, the combined organic layers were dried over MgSO4, concentrated in vacuo, and the residue purified on silica gel to afford 2-[({[(3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]pyrimidin-4-amine [150 mg, yield 3%].

후처리

  1. customovernight
  2. customat room temperature
  3. extractionAfter dilution of the reaction mixture with water and extraction with ethyl acetate
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified on silica gel

출처 및 근거

ORD 기록
ord-7f50f8d852cb4ebe8d9afd7c0a114a51
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981111B2

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