Pyridine → 4-chloro-3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 72719

反応式

HRID 72719 の反応式
Cl[C:2]1[C:7]([C:8]([C:10]2[N:14]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=3)[CH:13]=[N:12][CH:11]=2)=O)=[C:6]([Cl:23])[N:5]=[CH:4][N:3]=1.[CH3:24][NH:25][NH2:26].N1C=CC=CC=1>C(#N)C>[Cl:23][C:6]1[N:5]=[CH:4][N:3]=[C:2]2[N:25]([CH3:24])[N:26]=[C:8]([C:10]3[N:14]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21][CH3:22])=[CH:17][CH:16]=4)[CH:13]=[N:12][CH:11]=3)[C:7]=12

参加物

5

反応物 3

HCID 1049PyridineHCID 6061MethylhydrazineHCID 86712567(4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanone

生成物 1

HCID 867125684-chloro-3-[1-(4-ethylphenyl)-1H-imidazol-5-yl]-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

A solution of (4,6-dichloropyrimidin-5-yl)[1-(4-ethylphenyl)-1H-imidazol-5-yl]methanone (C21) (136 mg, 0.392 mmol) in acetonitrile (3 mL) was added to a solution of methylhydrazine (18.1 mg, 0.393 mmol) in acetonitrile (3 mL). After addition of pyridine (41 mg, 0.52 mmol), the reaction mixture was stirred at room temperature for 1 hour and then concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in heptane) afforded the product, along with recovered starting material (35 mg, 0.10 mmol). Yield: 81 mg, 0.24 mmol, 61% (82% based on recovered starting material). LCMS m/z 339.0 (M+1). 1H NMR (500 MHz, CDCl3) δ 1.21 (t, J=7.6 Hz, 3H), 2.62 (q, J=7.6 Hz, 2H), 4.11 (s, 3H), 7.11-7.15 (m, 4H), 7.52 (d, J=0.8 Hz, 1H), 7.85 (d, J=1.0 Hz, 1H), 8.73 (s, 1H).

後処理

  1. concentrationconcentrated in vacuo
  2. customPurification via silica gel chromatography (Gradient: 0% to 20% ethyl acetate in heptane)
  3. customafforded the product
  4. customalong with recovered
  5. customYield: 81 mg, 0.24 mmol, 61% (82% based on recovered starting material)

出典と根拠

ORDレコード
ord-2943dbf91fcb497085f59aa9a245855d
出典データセット
uspto-grants-2014_09
特許番号
US08829010B2

関連ノート

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