Ethyl Acetate → HCID 58994234, compound

HRID 12664Notes

Reaction equation

HRID 12664 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH:10]=[C:9]([C:11]2[S:12][CH:13]=[CH:14][C:15]=2[CH3:16])[C:8](=[O:17])[NH:7][C:6]1=[O:18].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C>C1COCC1>[CH3:16][C:15]1[CH:14]=[CH:13][S:12][C:11]=1[C:9]1[C:8](=[O:17])[NH:7][C:6](=[O:18])[N:5]([CH2:4][CH2:3][CH:2]=[O:1])[CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 589941881-(3-Hydroxypropyl)-5-(3-methylthiophen-2-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 58994234HCID 58994234, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(3-Hydroxy-propyl)-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 28.36 mg, 0.13 mmol) was dissolved in dry THF (5 mL), the solution was cooled to 0° C. and then Dess-Martin periodinane (97 mg, 0.22 mmol) was added under nitrogen. The mixture was stirred at room temperature for 1.5 hours. Ethyl acetate was added and the solution was 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 (7-3) to give 17 mg of the title compound (50% yield).

Workup

  1. washthe solution was 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 (7-3)

Sources & evidence

ORD record
ord-6cb627a6ee604040bc5f5bdbf9aeff00
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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