Lithium Hexamethyldisilazide → HCID 57747371、化合物

HRID 386624ノート

反応式

HRID 386624 の反応式
[Br:1][C:2]1[CH:33]=[C:32]([CH3:34])[C:5]([O:6][C:7]2[C:8]3[NH:31][CH:30]=[CH:29][C:9]=3[N:10]=[C:11]([N:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:12]=2)=[C:4]([CH3:35])[CH:3]=1.[Li+].[CH3:37][Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:35])[C:5]([O:6][C:7]2[C:8]3[N:31]([CH3:37])[CH:30]=[CH:29][C:9]=3[N:10]=[C:11]([N:13]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[N:12]=2)=[C:32]([CH3:34])[CH:33]=1

参加物

4

反応物 2

HCID 2733832Lithium HexamethyldisilazideHCID 57747399HCID 57747399、化合物

生成物 1

HCID 57747371HCID 57747371、化合物収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a cold mixture of tert-butyl 4-(4-bromo-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (0.81 g, 1.5 mmol) in THF (5 ml) at −78° C. was added a solution of LiHMDS (1M, 2 ml, 2 mmol). The mixture was warmed to 0° C. over 2 hours and then was cooled to −78° C. Idomethane (0.37 ml, 6 mmol) was added and the mixture was warmed to room temperature over 2 hours and then stirred at this temperature for an additional 2 hours. The mixture was washed with brine, extracted with ethyl acetate (×3). The organic layers were combined dried over MgSO4 and concentrated to dryness. The crude material was purified by chromatography on silica to obtain the title compound (0.782 g, 1.42 mmol, 95%). 1H NMR (CDCl3, 400 MHz) δ 1.32 (s, 9H), 2.07 (s, 6H), 4.18 (s, 3H), 6.65 (d, J=3.8 Hz, 1H), 7.15 (d, J=8.8 Hz, 2H), 7.21 (s, 2H), 7.37 (d, J=3.8 Hz, 1H), 7.49 (d, J=8.8, 2H).

後処理

  1. temperaturewas cooled to −78° C
  2. additionIdomethane (0.37 ml, 6 mmol) was added
  3. temperaturethe mixture was warmed to room temperature over 2 hours
  4. washThe mixture was washed with brine
  5. extractionextracted with ethyl acetate (×3)
  6. dry with materialThe organic layers were combined dried over MgSO4
  7. concentrationconcentrated to dryness
  8. customThe crude material was purified by chromatography on silica

出典と根拠

ORDレコード
ord-8f02c6e9664c4a229a53b64e6964bd84
出典データセット
uspto-grants-2013_02
特許番号
US08372852B2

反応ノート

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