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

HRID 875196ノート

反応式

HRID 875196 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

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%].

後処理

  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

出典と根拠

ORDレコード
ord-7f50f8d852cb4ebe8d9afd7c0a114a51
出典データセット
uspto-grants-2015_03
特許番号
US08981111B2

反応ノート

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