O-Toluidine → N-(4-hydroxyphenyl)-6-(o-tolylamino)pyrimidine-4-carboxamide

HRID 1746705

反応式

HRID 1746705 の反応式
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=2C)=[O:9])[CH:3]=1.C(N(C(C)C)C(C)C)C.[NH2:28][C:29]1[C:30]([CH3:35])=[CH:31][CH:32]=[CH:33][CH:34]=1>C(O)C>[OH:17][C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:8]([C:4]2[CH:3]=[C:2]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])[N:7]=[CH:6][N:5]=2)=[O:9])=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 7242O-ToluidineHCID 81531DiisopropylethylamineHCID 594471056-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide

生成物 1

HCID 25182757N-(4-hydroxyphenyl)-6-(o-tolylamino)pyrimidine-4-carboxamide

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
160 °C

実験手順

A solution of 6-chloro-N-(4-hydroxy-2-methylphenyl)pyrimidine-4-carboxamide, Intermediate 7 (50.0 mg; 0.20 mmol) in ethanol (3 mL) was treated with N-ethyldiisopropylamine (69 μl; 0.4 mmol) and o-toluidine (Fluka, 21.5 μl; 0.20 mmol). The reaction mixture was heated at 160° C. for 3 hours under microwave irradiation. The solvents were removed in vacuo, EtOAc was added and the organic phase was washed with a citric acid solution, dried over magnesium sulfate then evaporated in vacuo. The crude product was purified by column chromatography (silica), eluting with cyclohexane containing an increasing amount of EtOAc. The title compound was obtained as a yellow solid.

後処理

  1. customThe solvents were removed in vacuo, EtOAc
  2. additionwas added
  3. washthe organic phase was washed with a citric acid solution
  4. dry with materialdried over magnesium sulfate
  5. customthen evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica)
  7. washeluting with cyclohexane containing an increasing amount of EtOAc

出典と根拠

ORDレコード
ord-30f70ff972404c0688d1b966d09d51d7
出典データセット
uspto-grants-2015_10
特許番号
US09150519B2

関連ノート

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