Diisopropylethylamine → Ethyl [4-({butyl[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino}methyl)-2-ethylphenoxy]acetate

HRID 1269668노트

반응식

HRID 1269668 반응식
[CH2:1]([NH:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH2:20][CH3:21])[CH:8]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.Cl[C:32]1[C:37]([CH3:38])=[C:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:35]=[CH:34][N:33]=1>C(Cl)Cl>[CH2:1]([N:5]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH2:20][CH3:21])[CH:8]=1)[C:32]1[C:37]([CH3:38])=[C:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:35]=[CH:34][N:33]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 184484024-Chloro-5-methyl-6-(4-methylphenyl)pyrimidineHCID 58622897Ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate

생성물 1

HCID 58622843Ethyl [4-({butyl[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino}methyl)-2-ethylphenoxy]acetate수율 18.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
100 °C

실험 절차

A mixture of ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate (0.23 g, 0.78 mmol), N,N-diisopropylethylamine (0.18 mL, 1.05 mmol) and 4-chloro-5-methyl-6-(4-methylphenyl)pyrimidine (0.114 g, 0.52 mmol) were heated at 100° C. in a sealed reactivial for 18 h. After this time the reactivial was allowed to cool to room temperature and the residue dissolved in CH2Cl2 (50 mL) and washed with water (10 mL) and brine (10 mL). The organic extract was separated by hydrophobic frit and evaporated. Purification by Biotage™ chromatography (Silica, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (46 mg).

후처리

  1. temperatureto cool to room temperature
  2. washwashed with water (10 mL) and brine (10 mL)
  3. extractionThe organic extract
  4. customwas separated by hydrophobic frit
  5. customevaporated
  6. customPurification by Biotage™ chromatography (Silica, 40 g)
  7. washeluting 9:1 cyclohexane

출처 및 근거

ORD 기록
ord-56677ac0fd02454c999dd14387ff9aea
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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