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

HRID 12703

반응식

HRID 12703 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f8171c7006b0492aa5e0fccdfb9481a4
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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