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Tetrahydrofuran → Tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 522692
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HRID 522692 반응식
[C:1]([C:9]1[CH:10]=[N:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[N:13][CH:14]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]1COCC1>>[C:2]1([C:1]([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)=[CH2:28])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

3

반응물 2

HCID 8028TetrahydrofuranHCID 118022456Tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate

생성물 1

HCID 118022644Tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate수율 89%

실험 절차

The above solution was added to a solution of tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate (1 g, 2.7 mmol) in dry THF (20 mL) at 0° C., and the reaction solution was stirred at room temperature for 2 h. The reaction was quenched by water (20 mL) and extracted with ethyl acetate (200 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography eluting with petroleum ether:ethyl acetate 10:1 to give tert-butyl 4-(5-(1-phenylvinyl)pyrimidin-2-yl)piperazine-1-carboxylate (890 mg, 89%) as a white solid. MS (ES+) C21H26N4O2 requires: 366, found: 367 [M+H]+.

후처리

  1. customThe reaction was quenched by water (20 mL)
  2. extractionextracted with ethyl acetate (200 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with petroleum ether:ethyl acetate 10:1

출처 및 근거

ORD 기록
ord-6bff7d5a1eef4e638c373944b3eb5eb2
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09334263B2

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