Cesium fluoride → 4-(5-Pyrimidin-2-yl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1038033

반응식

HRID 1038033 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16](Br)=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1)CCC.[F-].[Cs+]>C(PC(C)(C)C)(C)(C)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][C:16]([C:25]3[N:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[CH:17][N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 34180719Tert-butyl 4-(5-bromo-1,3-thiazol-2-yl)piperazine-1-carboxylate

생성물 1

HCID 595113564-(5-Pyrimidin-2-yl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 86614436Di-t-butylphosphine palladium촉매

반응 조건

온도
90 °C

실험 절차

A round bottom flask containing 4-(5-bromo-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert-butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90° C. overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

후처리

  1. customwas degassed three times with Ar
  2. additionDioxane was added
  3. customthe formed reaction mixture
  4. filtrationThen the reaction mixture was filter through celite
  5. customthe solvent was removed under vacuum and crude product

출처 및 근거

ORD 기록
ord-0fa3a91681314b309e1665df91b7da55
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546404B2

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