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Sodium Carbonate → 4-(2-Fluoro-phenyl)-2-methylsulfanyl-pyrimidine

HRID 1514431
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HRID 1514431 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 971134-Chloro-2-methylthiopyrimidineHCID 27343542-Fluorophenylboronic acid

생성물 1

HCID 592427874-(2-Fluoro-phenyl)-2-methylsulfanyl-pyrimidine수율 90%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 10311-Propanol용매

실험 절차

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine (1.00 g, 6.22 mmol), 2-fluoro-phenyl-boronic acid (1.04 g, 6.84 mmol), Na2CO3 (790 mg, 7.45 mmol), triphenylphosphine (163 mg, 0.62 mmol) in nPrOH (50 ml), Pd(OAc)2 (42 mg, 0.187 mmol) was added and the mixture was refluxed for 3 hours. The solvent was evaporated under vacuum, and the crude was dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5) to give the title compound (1.23 g, 90% yield).

후처리

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customthe crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5)

출처 및 근거

ORD 기록
ord-d75b0e9e055c4634b925646c60f3d7e8
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08222266B2

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