Triethylamine → (R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2,4-dichloro-pyrimidin-5-yl-methyl)-1-(4-ethyl-phenyl)-urea

HRID 1243223ノート

反応式

HRID 1243223 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.[N+](C1C=CC([O:28][C:29](=O)[NH:30][C@H:31]([CH3:41])[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])=CC=1)([O-])=O.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:37]([Si:34]([CH3:36])([CH3:35])[O:33][CH2:32][C@H:31]([NH:30][C:29](=[O:28])[N:10]([CH2:9][C:5]1[C:6]([Cl:8])=[N:7][C:2]([Cl:1])=[N:3][CH:4]=1)[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=1)[CH3:41])([CH3:40])([CH3:39])[CH3:38]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 11426039(2,4-Dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)-amineHCID 58715060(R)-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-carbamic acid 4-nitro-phenyl ester

生成物 1

HCID 11488861(R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2,4-dichloro-pyrimidin-5-yl-methyl)-1-(4-ethyl-phenyl)-urea

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of (2,4-dichloro-pyrimidin-5-yl-methyl)-(4-ethyl-phenyl)amine (620 mg, 2.19 mmol) (from Example 38c supra), (R)-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-carbamic acid 4-nitro-phenyl ester (778 mg, 2.19 mmol) (from Example 38b supra) and triethylamine (0.93 mL, 6.6 mmol) (Allied Signal) in toluene (20 mL) was heated at reflux for 48 hours. The reaction mixture was quenched at room temperature with 1 N aqueous hydrochloric acid then extracted with ethyl acetate. The combined organic layers were successively washed with 1 N aqueous sodium hydroxide solution and brine, then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to give (R)-3-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(2,4-dichloro-pyrimidin-5-yl-methyl)-1-(4-ethyl-phenyl)-urea. (Yield 383 mg, 36%).

後処理

  1. temperatureat reflux for 48 hours
  2. customThe reaction mixture was quenched at room temperature with 1 N aqueous hydrochloric acid
  3. extractionthen extracted with ethyl acetate
  4. washThe combined organic layers were successively washed with 1 N aqueous sodium hydroxide solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-5a39a2a4222c4a658283050c8d385366
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

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