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

HRID 12657
Notes
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Reaction equation

HRID 12657 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-7803cddafcb04961b30e4533461f82af
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07727988B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes