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Ethyl Acetate → 1-(3,3-Dimethoxy-propyl)-5-(3-fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione

HRID 12697
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HRID 12697 반응식
Cl.[F:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[C:10](=[O:16])[NH:11][C:12](=[O:15])[NH:13][CH:14]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH:26]([O:29][CH3:30])[O:27][CH3:28].C(OCC)(=O)C>CN(C=O)C>[CH3:28][O:27][CH:26]([O:29][CH3:30])[CH2:25][CH2:24][N:13]1[CH:14]=[C:9]([C:8]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[F:2])[C:10](=[O:16])[NH:11][C:12]1=[O:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 686942765-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride

생성물 1

HCID 589941561-(3,3-Dimethoxy-propyl)-5-(3-fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione수율 22%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

5-(3-Fluoro-pyridin-4-yl)-1H-pyrimidine-2,4-dione hydrochloride (Prep 67, 243 mg, 1.1 mmol) was dissolved in DMF (2 ml). K2CO3 (153 mg, 1.1 mmol) was added and the mixture was stirred at room temperature for 1 hour. 3-Bromo-1,1dimethoxy-propane (225 mg, 1.11 mmol) was then added and after stirring the reaction at room temperature for 48 hours, the reaction was left at 4° C. for 17 days. Ethyl acetate was then added and the mixture washed with water and brine. The organic phase was dried (Na2SO4) and evaporated. The residue was purified by flash chromatography with DCM-MeOH—NH4OH 98-2-0.2 to afford 75 mg of the title compound (22% yield).

후처리

  1. stirringafter stirring
  2. customthe reaction at room temperature for 48 hours
  3. waitthe reaction was left at 4° C. for 17 days
  4. washthe mixture washed with water and brine
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography with DCM-MeOH—NH4OH 98-2-0.2

출처 및 근거

ORD 기록
ord-139880581b8140598e60dce3f19e2b8f
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07727988B2

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