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Sodium Carbonate → 5-Biphenyl-4-yl-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine

HRID 19607
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HRID 19607 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[N:16]=[CH:17][CH:18]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[N:16]=[CH:17][CH:18]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2회HCID 673194195-(4-Iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine2회

생성물 1

HCID 673186175-Biphenyl-4-yl-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine수율 77.1%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

실험 절차

Under an inert gas atmosphere is dissolved 5-(4-iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine (compound D1)(0.45 g) and phenylboronic acid (0.35 g) in dimethoxyethane. To this solution are added bis-(triphenylphosphine)-palladium(II) chloride (0.19 mmol) and an aqueous sodium carbonate solution (2M, 6 ml). The reaction mixture is heated to reflux for 4.5 h. After 1 h further phenylboronic acid (0.2 g) is added in order to complete the reaction. The mixture is diluted with ethyl acetate and filtered over silica gel. The product is partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate (5%), the organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A nearly colorless solid (0.3 g) in 50% yield is obtained.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4.5 h
  3. customthe reaction
  4. filtrationfiltered over silica gel
  5. customThe product is partitioned between ethyl acetate
  6. dry with materialan aqueous solution of sodium bicarbonate (5%), the organic phase is dried over sodium sulfate
  7. customthe crude product is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-70998479748949489811774a11e6c067
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745446B2

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