Diethyl Ether → 3-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehyde

HRID 12657

반응식

HRID 12657 반응식
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:8](=[O:15])[NH:7][C:6]1=[O:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC>C1COCC1>[F:13][C:11]([F:12])([F:14])[C:9]1[C:8](=[O:15])[NH:7][C:6](=[O:16])[N:5]([CH2:4][CH2:3][CH:2]=[O:1])[CH:10]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 589942071-(3-Hydroxy-propyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

생성물 1

HCID 589941853-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehyde수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

1-(3-Hydroxy-propyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep20, 100 mg, 0.42 mmol) was dissolved in dry THF (5 mL), the solution was then cooled to 0° C. and Dess-Martin periodinane (300 mg, 0.71 mmol) was added. The mixture was stirred at 0° C. for 1.5 hours. Et2O was added and the mixture washed with aqueous saturated NaHCO3 solution. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-1) to give 50 mg of title compound (68% yield).

후처리

  1. washthe mixture washed with aqueous saturated NaHCO3 solution
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-1)

출처 및 근거

ORD 기록
ord-7803cddafcb04961b30e4533461f82af
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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