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

HRID 522693
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HRID 522693 반응식
[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
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HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 118022644Tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate

생성물 1

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

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran
용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-05b0bdd290d942239bcea83c4f5ab51d
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09334263B2

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