Sodium Carbonate → 3-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile

HRID 12726

반응식

HRID 12726 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.[C:14]([C:16]1[C:21](Br)=[CH:20][CH:19]=[CH:18][N:17]=1)#[N:15].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]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:21]2[C:16]([C:14]#[N:15])=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 8176943-Bromopyridine-2-carbonitrileHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

생성물 1

HCID 589942323-(2,4-Dimethoxy-pyrimidin-5-yl)-pyridine-2-carbonitrile수율 79.5%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

2,4-Dimethoxy-pyrimidine-5-boronic acid (1 g, 5.46 mmol) was dissolved in degassed n-PrOH (30 ml) and then 2-cyano-3-bromopyridine (950 mg, 5.19 mmol), Na2CO3 (1.65 g, 15.56 mmol), PPh3 (393 mg, 1.5 mmol) and Pd(OAc)2 (114 mg, 0.51 mmol) were added. The suspension was stirred at reflux for 3 hours. After cooling, the solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with iPrOH to give 1 g of the title compound as a white powder (76% yield).

후처리

  1. temperatureat reflux for 3 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under vacuum
  4. customthe crude was partitioned between water and ethyl acetate
  5. washThe organic phase washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was triturated with iPrOH

출처 및 근거

ORD 기록
ord-479b3529179947c7ae9108e5afb47566
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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