Ethyl Acetate → HCID 53468672、化合物

HRID 2401170ノート

反応式

HRID 2401170 の反応式
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

参加物

7

反応物 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

生成物 1

HCID 53468672HCID 53468672、化合物収率 45.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1288cb7cdbf4a73815657f5c4b9cf6a
出典データセット
uspto-grants-2014_08
特許番号
US08796284B2

反応ノート

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