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

HRID 12659
Notes
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Reaction equation

HRID 12659 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2d9ddf4e5bc948ea8390a84b8afb5556
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