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4-Benzyl-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid methoxy-methyl-amide → 1-(4-Benzyl-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)-2-(4-methylphenyl)ethanone

HRID 63762
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인쇄 미리보기

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HRID 63762 반응식
CON(C)[C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([CH3:16])([CH3:15])[CH2:13][CH:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[N:11]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10]=12)=[O:5].[CH3:31][C:32]1[CH:40]=[CH:39][C:35]([CH2:36][Mg]Cl)=[CH:34][CH:33]=1>C1COCC1>[CH2:23]([N:11]1[CH:12]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][C:14]([CH3:16])([CH3:15])[N:9]2[N:8]=[CH:7][C:6]([C:4](=[O:5])[CH2:31][C:32]3[CH:40]=[CH:39][C:35]([CH3:36])=[CH:34][CH:33]=3)=[C:10]12)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 576317744-Benzyl-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxylic acid methoxy-methyl-amideHCID 178425359HCID 178425359, 화합물

생성물 1

HCID 576320601-(4-Benzyl-7,7-dimethyl-5-phenyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidin-3-yl)-2-(4-methylphenyl)ethanone수율 89%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 0.65 g (1.61 mmol) of 3 dissolved in 20 mL of THF was added 6.4 mL (3.2 mmol) of a 0.5 M solution of 4-methylbenzylmagnesium chloride in THF via syringe over 10 min. After stirring at room temperature for 1 h, the reaction was quenched by addition of approximately 2 mL of saturated aqueous ammonium chloride. The reaction was then diluted with AcOEt and dried over sodium sulfate. Filtering the solution through a short plug of silica gel and concentrating in vacuo provided the crude product as an oil. Purification of this oil by flash chromatography eluting with 75% hexanes/AcOEt gave 0.64 g (89%) of the title compound as a white foam. MS Calcd.: 449. Found: 450 (M+H).

후처리

  1. customthe reaction was quenched by addition of approximately 2 mL of saturated aqueous ammonium chloride
  2. additionThe reaction was then diluted with AcOEt
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltering the solution through a short plug of silica gel
  5. concentrationconcentrating in vacuo
  6. customprovided the crude product as an oil
  7. customPurification of this oil by flash chromatography
  8. washeluting with 75% hexanes/AcOEt

출처 및 근거

ORD 기록
ord-2c62dc13002a4f318261a260526e53ff
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09447100B2

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