Butylethylamine → [[6-(Butyl-N-ethylamino)-2-methylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl ester

HRID 1737672노트

반응식

HRID 1737672 반응식
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]([C:16]1[CH:21]=[C:20](Cl)[N:19]=[C:18]([CH3:23])[N:17]=1)[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15])[CH3:2].[CH2:25]([NH:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]([C:16]1[CH:21]=[C:20]([N:29]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH3:31])[N:19]=[C:18]([CH3:23])[N:17]=1)[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15])[CH3:2]

참가 물질

4

반응물 2

HCID 25914Butylethylamine2회HCID 86596480[(6-Chloro-2-methyl-pyrimidin-4-yl)(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl ester

생성물 1

HCID 69587593[[6-(Butyl-N-ethylamino)-2-methylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl ester수율 122.2%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
135 °C

실험 절차

A mixture of [(6-chloro-2-methylpyrimidin-4-yl)-(2,4,6-trimethylpheny)-amino]-acetic acid ethyl ester (85 mg, 0.244 mmol) and N-butyl-ethylamine (0.17 ml, 1.1 mmol) in 4 ml DMSO was heated at 135° C. for 15 hours. An additional 1 ml of N-butyl-ethylamine was added and the reaction was heated at that temperature for an additional 15 hours (tic showed no starting material). The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 123 mg of a light amber oil. The oil was purified through silica gel chromatotron using 5% ethyl acetate in hexane as eluent to give 92 mg (91%) of the title compound as a white glass. 1H NMR (CDCl3) δ6.94 (s, 2H), 4.69 (s, 1H), 4.23 (s, 2H), 4.22 (q, 2H), 3.35 (q, 2H), 3.15 (t, 2H), 2.36 (s, 3H), 2.31 (s, 3H), 2.21 (s, 6H), 1.3-1.5 (m, 2H), 1.34 (t, 3H), 1.1-1.3 (m, 2H), 1.01 (t, 3H), 0.80 (t, 3H) ppm.

후처리

  1. temperaturethe reaction was heated at that temperature for an additional 15 hours (tic
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d45bafd9f59e4d0aaaefa364f2381344
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962479

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