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

HRID 1269668ノート

反応式

HRID 1269668 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-56677ac0fd02454c999dd14387ff9aea
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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