Ethyl Acetate → HCID 53468672, 화합물

HRID 2401170노트

반응식

HRID 2401170 반응식
Br[C:2]1[C:3]([NH2:18])=[N:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.[CH3:19][N:20]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[N:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>O1CCOCC1.O>[CH3:19][N:20]1[CH:24]=[C:23]([C:2]2[C:3]([NH2:18])=[N:4][C:5]([N:13]3[CH:17]=[CH:16][CH:15]=[N:14]3)=[N:6][C:7]=2[N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)[CH:22]=[N:21]1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 534669585-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine

생성물 1

HCID 53468672HCID 53468672, 화합물수율 45.3%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 0.1 g (0.33 mmol) of 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4-amine (Example 1), 0.10 g (0.49 mmol) of 1-methylpyrazole-4-boronic acid pinacol ester, 0.23 (0.72 mmol) of cesium carbonate and 5 mg (6.5 μmol) of [1,1′-Bis(diphenylphosphino) ferrocene]dichloropaladium (II) dichloromethane complex in 3 ml dioxane and 0.5 ml of water were irradiated with microwaves at 140° C. for 30 min. After cooling to room temperature ethyl acetate was added and filtered by celite. The solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine. The organic layer was separated, dried with MgSO4 and concentrated. The residue was purified by column chromatography with silica gel and methylene chloride and methanol as eluent to give 45.5 mg (45.3%) of the desired product.

후처리

  1. customwere irradiated with microwaves at 140° C. for 30 min
  2. additionwas added
  3. filtrationfiltered by celite
  4. extractionThe solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine
  5. customThe organic layer was separated
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography with silica gel and methylene chloride and methanol as eluent

출처 및 근거

ORD 기록
ord-a1288cb7cdbf4a73815657f5c4b9cf6a
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796284B2

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