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

HRID 12657

反应方程式

HRID 12657 反应方程式
[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

参与物

5

反应物 3

HCID 3283乙醚HCID 159087戴斯-马丁氧化剂HCID 589942071-(3-Hydroxy-propyl)-5-trifluoromethyl-1H-pyrimidine-2,4-dione

产物 1

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

试剂、催化剂与溶剂 1

HCID 8028四氢呋喃溶剂

反应条件

温度
0 °C

实验过程

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).

后处理

  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)

来源与证据

ORD记录
ord-7803cddafcb04961b30e4533461f82af
来源数据集
uspto-grants-2010_06
专利号
US07727988B2

关联笔记

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