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Sulfoxonium, trimethyl-, iodide (1:1) → Tert-butyl 4-(5-(1-phenylcyclopropyl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 522693
ノート
印刷プレビュー

反応式

HRID 522693 の反応式
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]3)=[N:13][CH:14]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[CH3:29][S+](C)(C)=O>C1COCC1.CS(C)=O.C(OCC)(=O)C>[C:1]1([C:7]2([C:9]3[CH:14]=[N:13][C:12]([N:15]4[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]4)=[N:11][CH:10]=3)[CH2:29][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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

6

反応物 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 118022644Tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate

生成物 1

HCID 118023385Tert-butyl 4-(5-(1-phenylcyclopropyl)pyrimidin-2-yl)piperazine-1-carboxylate収率 10.5%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate (366 mg, 1.0 mmol) in THF (20 mL) was added trimethylsulfoxonium iodide (1.1 g 5.0 mmol) in dimethyl sulfoxide (7 mL). The reaction mixture was stirred at 80° C. for 4 days, and diluted with ethyl acetate (200 mL). The organic phase was washed with water (200 mL) and brine (100 mL), dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=20:1) to give tert-butyl 4-(5-(1-phenylcyclopropyl)pyrimidin-2-yl)piperazine-1-carboxylate (40 mg, 10%) as a yellow solid. MS (ES+) C22H28N4O2 requires: 380, found: 381 [M+H]+.

後処理

  1. washThe organic phase was washed with water (200 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=20:1)

出典と根拠

ORDレコード
ord-05b0bdd290d942239bcea83c4f5ab51d
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09334263B2

反応ノート

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