Sodium Carbonate → 5-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

HRID 12714

반응식

HRID 12714 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.[Cl:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][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]>[Cl:14][C:15]1[N:16]=[CH:17][C:18]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)=[CH:19][CH:20]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 43971762-Chloro-5-iodopyridine

생성물 1

HCID 589942255-(6-Chloro-pyridin-3-yl)-2,4-dimethoxy-pyrimidine

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

2,4-Dimethoxy-pyrimidine-5-boronic acid (1.14 g, 6.26 mmol) was dissolved in degassed n-PrOH (20 ml) and then 2-chloro-5-iodopyridine (1 g, 4.2 mmol), Na2CO3 (884 mg, 15.8 mmol), PPh3 (109 mg, 0.42 mmol) and Pd(OAc)2 (46 mg) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used in the next step without further purification (quantitative yield).

후처리

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-83a8359273f84a0e9c3c5ff492ad4420
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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