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6-(Bromomethyl)-4-chloroquinazoline → HCID 86757280、化合物

HRID 651632
ノート
印刷プレビュー

反応式

HRID 651632 の反応式
[CH3:1][N:2]([C@H:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23])[S:3]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[CH:7]=1)(=[O:5])=[O:4].[Li]N([Si](C)(C)C)[Si](C)(C)C.Br[CH2:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[CH:41][N:40]=[C:39]2[Cl:46]>C1COCC1>[Cl:46][C:39]1[C:38]2[C:43](=[CH:44][CH:45]=[C:36]([CH2:35][N:20]3[CH2:21][CH2:22][C@H:18]([N:2]([CH3:1])[S:3]([C:6]4[CH:15]=[CH:14][C:13]5[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=5)[CH:7]=4)(=[O:5])=[O:4])[C:19]3=[O:23])[CH:37]=2)[N:42]=[CH:41][N:40]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 219419376-(Bromomethyl)-4-chloroquinazolineHCID 54147218HCID 54147218、化合物HCID 178418261HCID 178418261、化合物

生成物 1

HCID 86757280HCID 86757280、化合物収率 52.1%

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 solution of 7-methoxynaphthalene-2-sulfonic acid methyl-(2-oxopyrrolidin-3-(S)-yl)-amide (0.35 g, 1.04 mmol) in THF (7 mL) at 0° C. is added LiN(SiMe3)2 (1 mL, 1 mmol, 1 M solution in THF). The solution is stirred at 0° C. for 40 minutes. After this time, 6-bromomethyl-4-chloro-quinazoline (0.24 g, 0.94 mmol) is added. The resulting solution is stirred for 4 hours. The reaction is quenched by the addition of a saturated NH4Cl solution. The solution is diluted with EtOAc and water. The layers are separated. The organic layer is washed with water and brine. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 20% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2 to give the title compound (0.25 g, 0.49 mmol) as a white solid.

後処理

  1. stirringThe resulting solution is stirred for 4 hours
  2. customThe reaction is quenched by the addition of a saturated NH4Cl solution
  3. additionThe solution is diluted with EtOAc and water
  4. customThe layers are separated
  5. washThe organic layer is washed with water and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by column chromatography
  10. washeluting with a gradient of 20% EtOAc/CH2Cl2 to 40% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-3acea98b22f4471a92a260e8f994e6c5
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06281227B1

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート