Sodium Carbonate → 2,4-Dimethoxy-5-(6-methyl-pyridin-3-yl)-pyrimidine

HRID 12687

반응식

HRID 12687 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:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=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]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:15]2[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:5][N:4]=1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 12010205-Bromo-2-methylpyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

생성물 1

HCID 589941672,4-Dimethoxy-5-(6-methyl-pyridin-3-yl)-pyrimidine수율 62%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

2,4-Dimethoxy-pyrimidine-5-boronic acid (commercially available from Aldrich, 830 mg, 4.5 mmol) was dissolved in degassed n-PrOH (10 mL) and then 3-bromo-6-methylpyridine (600 mg, 3.5 mmol), Na2CO3 (956 mg, 9 mmol), PPh3 (90 mg, 0.35 mmol) and Pd(OAc)2 (78 mg, 0.35 mmol) were added. The suspension was stirred at reflux for 1.5 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 purified by SCX cartridge washing with MeOH and then collecting the product with MeOH—NH4OH (95-5) to give 500 mg of the title compound (62% yield).

후처리

  1. temperatureat reflux for 1.5 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 purified by SCX cartridge
  7. washwashing with MeOH
  8. customcollecting the product with MeOH—NH4OH (95-5)

출처 및 근거

ORD 기록
ord-467f17a6508d4a118f67db9676324ab1
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

연결된 노트

불러오는 중…