[(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amine → HCID 178491934、化合物

HRID 1243186ノート

反応式

HRID 1243186 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C([Li])CCC.[C:24]([Si:28]([O:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([N:38]=[C:39]=[O:40])[CH2:34][CH2:33]1)([CH3:30])[CH3:29])([CH3:27])([CH3:26])[CH3:25]>O1CCCC1.C(OCC)(=O)C>[C:24]([Si:28]([CH3:30])([CH3:29])[O:31][C@H:32]1[CH2:37][CH2:36][C@H:35]([N:38]2[C:6]3=[N:7][C:2]([Cl:1])=[N:3][CH:4]=[C:5]3[CH2:9][N:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:39]2=[O:40])[CH2:34][CH2:33]1)([CH3:27])([CH3:26])[CH3:25]

参加物

6

反応物 3

HCID 21939303[(2,4-Dichloropyrimidin-5-yl)methyl](4-methoxyphenyl)amineHCID 178418339ButyllithiumHCID 178455365HCID 178455365、化合物

生成物 1

HCID 178491934HCID 178491934、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

To a solution of [(2,4-dichloropyrimidin-5-yl)methyl](4-methoxy-phenyl)amine (1.0 g, 3.52 mmol) (from Example 1d supra) in tetrahydrofuran (50 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes, 1.7 mL, 4.22 mmol) (Aldrich). After stirring at −78° C. for 20 minutes, tert-butyl-(trans-4-isocyanato-cyclohexyloxy)-dimethyl-silane (1.1 g, 4.22 mmol) (from Example 17b supra) was added. The mixture was stirred at −70° C. for 1 hour and then at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate-hexanes (3:7 then 2:3) to give 1-[trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-7-chloro-3-(4-methoxy-phenyl)-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one. (Yield 0.61 g, 34%).

後処理

  1. stirringThe mixture was stirred at −70° C. for 1 hour
  2. waitat room temperature for 3 hours
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate-hexanes (3:7

出典と根拠

ORDレコード
ord-c9def535b167420790bb61f77ab242e4
出典データセット
uspto-grants-2006_10
特許番号
US07115740B2

反応ノート

読み込み中…