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Potassium Iodide → 1-[1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1499842
ノート
印刷プレビュー

反応式

HRID 1499842 の反応式
[Br:1][C:2]1[C:3]([CH3:14])=[C:4]([Cl:13])[CH:5]=[C:6]([CH:10](Cl)[CH3:11])[C:7]=1[O:8][CH3:9].[I:15][C:16]1[C:24]2[C:19](=[N:20][CH:21]=[N:22][C:23]=2[NH2:25])[NH:18][N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>CN(C)C=O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH:10]([N:18]2[C:19]3=[N:20][CH:21]=[N:22][C:23]([NH2:25])=[C:24]3[C:16]([I:15])=[N:17]2)[CH3:11])[CH:5]=[C:4]([Cl:13])[C:3]=1[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 866776443-Bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzeneHCID 178508725HCID 178508725、化合物

生成物 1

HCID 866777661-[1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethyl]-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
140 °C

実験手順

A mixture of 3-bromo-1-chloro-5-(1-chloroethyl)-4-methoxy-2-methylbenzene (0.60 g, 2.0 mmol, from Example 167, Step 3), 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (590 mg, 2.2 mmol, from AnaSpec), cesium carbonate (0.98 g, 3.0 mmol) and potassium iodide (30 mg, 0.2 mmol) in N,N-dimethylformamide (8 mL) was stirred at 140° C. for 1 h. The mixture was cooled down and then the solvent was completely removed. The residue was stirred with CH2Cl2 (30 mL) at room temperature for 20 min and then filtered. The filtrate was concentrated and the product (0.65 g, 63%) was purified by chromatography eluting with CH2Cl2/EtOAc (max. EtOAc 60%). LCMS calculated for C15H15BrClIN5O (M+H)+: m/z=521.9; Found: 521.9.

後処理

  1. temperatureThe mixture was cooled down
  2. customthe solvent was completely removed
  3. stirringThe residue was stirred with CH2Cl2 (30 mL) at room temperature for 20 min
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe product (0.65 g, 63%) was purified by chromatography
  7. washeluting with CH2Cl2/EtOAc (max. EtOAc 60%)

出典と根拠

ORDレコード
ord-2feff151c1c941c3bb37e0e82cbfc9bd
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09199982B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート