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

HRID 1746705

반응식

HRID 1746705 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-30f70ff972404c0688d1b966d09d51d7
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150519B2

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