4-Aminopyrimidine → 4-chloro-N-(pyrimidin-4-yl)quinoline-7-sulfonamide

HRID 1473413ノート

反応式

HRID 1473413 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19](OC3C(F)=C(F)C(F)=C(F)C=3F)(=[O:21])=[O:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([S:19]([NH:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][N:3]=3)(=[O:20])=[O:21])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 689584-AminopyrimidineHCID 2733832Lithium HexamethyldisilazideHCID 86687458Perfluorophenyl 4-chloroquinoline-7-sulfonate

生成物 1

HCID 866874614-chloro-N-(pyrimidin-4-yl)quinoline-7-sulfonamide収率 67.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A flask containing a solution of 4-aminopyrimidine (0.026 g, 0.268 mmol) and perfluorophenyl 4-chloroquinoline-7-sulfonate (from Step 2, Intermediate LLLL; 0.100 g, 0.244 mmol) in THF (1.220 ml) was cooled to −78° C. for 10 minutes, and then lithium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (0.488 ml, 0.488 mmol) was added dropwise. After 20 minutes, the reaction had gone to completion. The reaction mixture was quenched with aq ammonium chloride, and concentrated under a vacuum. A 2:1 mixture of DCM:H2O was added, the flask sonicated, and the solids filtered to yield 4-chloro-N-(pyrimidin-4-yl)quinoline-7-sulfonamide (0.053 g, 0.165 mmol, 67.7% yield) as a light brown solid (carried forward crude). m/z (ESI) 321.0 (M+H)+.

後処理

  1. customThe reaction mixture was quenched with aq ammonium chloride
  2. concentrationconcentrated under a vacuum
  3. additionA 2:1 mixture of DCM
  4. additionH2O was added
  5. customthe flask sonicated
  6. filtrationthe solids filtered

出典と根拠

ORDレコード
ord-82eb3998c80f42eb9221a4af2c845e92
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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