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

HRID 12659

반응식

HRID 12659 반응식
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:9](=[O:16])[NH:8][C:7]1=[O:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOCC>C1COCC1>[F:14][C:12]([F:13])([F:15])[C:10]1[C:9](=[O:16])[NH:8][C:7](=[O:17])[N:6]([CH2:5][CH2:4][CH2:3][CH:2]=[O:1])[CH:11]=1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 589942241-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

생성물 1

HCID 589941974-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-butyraldehyde수율 51.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

1-(4-Hydroxy-butyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione (Prep 23, 44 mg, 0.17 mmol) was dissolved in dry THF (5 mL), the solution was cooled to 0° C. and Dess-Martin periodinane (127 mg, 0.28 mmol) was added. The mixture was stirred at 0° C. for 1.5 hours. Et2O was added and the solution washed with aqueous saturated NaHCO3. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-1) to give 22 mg of the title compound (50% yield).

후처리

  1. washthe solution washed with aqueous saturated NaHCO3
  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-2d9ddf4e5bc948ea8390a84b8afb5556
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727988B2

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