N-Cyclohexylaniline → (5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amine

HRID 79113

反応式

HRID 79113 の反応式
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:10]1([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN1CCCC1=O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([N:16]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

参加物

5

反応物 2

HCID 74567N-CyclohexylanilineHCID 2899735-Bromo-2,4-dichloropyrimidine

生成物 1

HCID 58299589(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amine収率 24%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

5-Bromo-2,4-dichloro-pyrimidine (2.17 ml, 17.14 mmol) and cyclohexyl-phenyl-amine (2.0 g, 11.43 mmol) were dissolved in N-methylpyrrolidone (NMP) (25 ml), and this reaction was heated to 120° C. for 24 hours. The reaction was cooled to room temperature and diluted with ethyl acetate, washed with water and brine. The organic phase was dried using sodium sulfate and concentrated. Purification by flash chromatography (ethyl acetate/hexane) gave compound 37 as a yellow solid (855 mg, 24%). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.27 (1 H, s), 7.41 (3 H, m), 7.21 (2 H, m), 4.62 (1 H, m), 1.93 (2 H, d, J=10 Hz), 1.75 (2 H, d, J=10 Hz), 1.58 (1 H, d, J=10 Hz), 1.34 (2 H, m), 1.15 (2 H, m), 0.91 (1 H, m).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water and brine
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customPurification by flash chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-6e09e02edeb2407fa29c35bb3c7b1f63
出典データセット
uspto-grants-2014_09
特許番号
US08841312B2

関連ノート

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