2-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amine → 4-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amine

HRID 1500801ノート

反応式

HRID 1500801 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[C:5]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[CH:4][N:3]=1.[H][H]>C(O)C.[Pd]>[NH2:14][C:10]1[CH:9]=[C:8]([C:6]2[C:5]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=3)=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 2

HCID 866775212-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 866775204-(3-aminophenyl)-2-chloro-N-(3-fluorophenyl)pyrimidin-5-amine収率 100%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

2-Chloro-N-(3-fluorophenyl)-4-(3-nitrophenyl)pyrimidin-5-amine (50 mg, 0.145 mmol) was added to the palladium/carbon (10 mg, 0.015 mmol) in ethanol (25 mL) and the applied hydrogen gas at 8 psi for 2 h at rt. The reaction was monitored by TLC. After completion of the reaction, the reaction mixture was filtered through celite; the solvent was removed by vacuum; and the crude material was purified by flash chromatography (2% CH3OH/DCM) to yield the title compound (35 mg, 0.145 mmol) as a solid. 1H NMR: (CDCl3, 400 MHz): δ 8.40 (s, 1H), 7.65 (m, 1H), 7.27-7.17 (m, 4H), 7.13-7.09 (m, 2H), 6.77 (m, 1H), 6.68 (m, 1H). ESI-MS: m/z 315.0 [M+H]+.

後処理

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite
  3. customthe solvent was removed by vacuum
  4. customand the crude material was purified by flash chromatography (2% CH3OH/DCM)

出典と根拠

ORDレコード
ord-d5e1155fcca64f28b432e3a6f35f39b7
出典データセット
uspto-grants-2015_12
特許番号
US09206176B2

反応ノート

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