Sodium Carbonate → 2,4-Ditert-butoxy-5-(3-methyl-2-thienyl)pyrimidine

HRID 12660

반응식

HRID 12660 반응식
[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9](B(O)O)=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:21]1[S:22][CH:23]=[CH:24][C:25]=1[CH3:26].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]>[C:1]([O:5][C:6]1[N:11]=[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([C:21]2[S:22][CH:23]=[CH:24][C:25]=2[CH3:26])=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 843142-Bromo-3-methylthiopheneHCID 2735950(2,4-Di-tert-butoxypyrimidin-5-yl)boronic acid

생성물 1

HCID 44586132,4-Ditert-butoxy-5-(3-methyl-2-thienyl)pyrimidine수율 32%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 10311-Propanol용매

실험 절차

2,4-Di-tert-butoxy-pyrimidine-5-boronic acid (500 mg, 1.75 mmol) was dissolved in n-PrOH (5 mL) and then 2-bromo-3-methylthiophene (236 μl, 2.1 mmol), Na2CO3 (556 mg, 5.25 mmol), PPh3 (133 mg, 0.52 mmol) and Pd(OAc)2 (40 mg, 0.17 mmol) were added. The suspension was stirred at reflux for 2.5 hours. The solvent was evaporated and the crude was dissolved in water and extracted with Et2O. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99) to give 170 mg of the title compound as a white solid (32% yield).

후처리

  1. temperatureat reflux for 2.5 hours
  2. customThe solvent was evaporated
  3. dissolutionthe crude was dissolved in water
  4. extractionextracted with Et2O
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-99)

출처 및 근거

ORD 기록
ord-6a27ead10db740a4ac7fefbba65f9c12
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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