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Potassium Carbonate → 8-Ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

HRID 1753168
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인쇄 미리보기

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HRID 1753168 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[NH:27][CH2:26][CH2:25][N:10]2[C:11](=[O:24])[C:12]2[N:13]([C:15]([C:18]#[C:19][Si](C)(C)C)=[CH:16][CH:17]=2)[CH2:14]3)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[C:18]([C:15]1[N:13]2[CH2:14][C:9]3([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[NH:27][CH2:26][CH2:25][N:10]3[C:11](=[O:24])[C:12]2=[CH:17][CH:16]=1)#[CH:19]
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참가 물질

5

반응물 2

HCID 11430Potassium CarbonateHCID 6736846710a-(4-methoxyphenyl)-8-[(trimethylsilyl)ethynyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

생성물 1

HCID 866570858-Ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one수율 89%

시약·촉매·용매 2

HCID 887Methanol용매
HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 10a-(4-methoxyphenyl)-8-[(trimethylsilyl)ethynyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (84 mg, 0.22 mmol) in methanol (5 mL) was added potassium carbonate (60 mg, 0.43 mmol). The suspension was stirred at room temperature until the reaction was complete (monitored by LCMS). The solid was suspended in CH2Cl2, filtered and concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4, 12 g cartridge, CH2Cl2 3CV, gradient 0-10% MeOH in CH2Cl2 10CV). To give 8-Ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as a yellow solid (60 mg, yield 89%). ESI-MI m/z [M+H]+ 308.0.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto give a residue that
  4. customwas purified by flash chromatography (Biotage SP4, 12 g cartridge, CH2Cl2 3CV, gradient 0-10% MeOH in CH2Cl2 10CV)

출처 및 근거

ORD 기록
ord-47daf1b0e6684dbc8e8474a1a6959bb9
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09163029B2

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