Sodium Carbonate → 5-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidine

HRID 12703

反応式

HRID 12703 の反応式
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[N:16]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:21][C:17]1[N:16]=[C:15]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)[CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 6394382-Bromo-6-fluoropyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

生成物 1

HCID 589942165-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidine収率 57.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 10311-Propanol溶媒

実験手順

2,4-Dimethoxy-pyrimidine-5-boronic acid (966 mg, 5.3 mmol) was dissolved in degassed n-PrOH (60 ml) and then 2-bromo-6-fluoropyridine (850 mg, 4.8 mmol), Na2CO3 (1.676 g, 15.8 mmol), PPh3 (400 mg, 1.52 mmol) and Pd(OAc)2 (116 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 650 mg of the title compound as a white powder (52% yield).

後処理

  1. temperatureat reflux for 3 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated
  6. customThe crude was triturated with iPrOH

出典と根拠

ORDレコード
ord-f8171c7006b0492aa5e0fccdfb9481a4
出典データセット
uspto-grants-2010_06
特許番号
US07727988B2

関連ノート

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