Potassium Carbonate → HCID 57839072、化合物

HRID 732955

反応式

HRID 732955 の反応式
Cl[C:2]1[C:7]([CH:8]=[O:9])=C[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1.[Cl:16][C:17]1[CH:18]=[C:19](B(O)O)[C:20]([CH3:23])=[CH:21][CH:22]=1.[C:27]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:7]([CH:8]=[O:9])=[CH:2][N:3]=[C:4]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:5]=2)=[C:19]([CH3:27])[CH:18]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 57839061HCID 57839061、化合物

生成物 1

HCID 57839072HCID 57839072、化合物収率 88.7%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
85 °C

実験手順

To a stirred solution of 4-chloro-2-phenylpyrimidine-5-carbaldehyde (50 mg, 0.23 mmol) and 4-chloro-o-toluene boronic acid (48 mg, 0.29 mmol) in dioxane (1 mL) and H2O (0.5 mL) was added Pd(PPh3)4 (26.5 mg, 0.02 mmol), K2CO3 (126.5 mg, 0.92 mmol). The reaction was heated to 85° C. for 6 hrs. After concentration under reduced pressure, the residue was diluted with EtOAc (10 mL) and the organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give the crude product (70 mg). The crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane) to give 4-(4-chloro-2-methylphenyl)-2-phenylpyrimidine-5-carbaldehyde (63 mg, 75%) as a white solid.

後処理

  1. concentrationAfter concentration under reduced pressure
  2. additionthe residue was diluted with EtOAc (10 mL)
  3. washthe organic layer was washed with saturated NH4Cl solution (10 mL), and brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product (70 mg)
  8. customThe crude product was purified by flash chromatography (silica gel, 20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-d8a06cc992f54305bf7417ba9ab58325
出典データセット
uspto-grants-2009_09
特許番号
US07589088B2

関連ノート

読み込み中…