Ethyl Acetate → HCID 58994229, compound

HRID 12666Notes

Reaction equation

HRID 12666 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]2[S:13][CH:14]=[CH:15][C:16]=2[CH3:17])[C:9](=[O:18])[NH:8][C:7]1=[O:19].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)(=O)C>C(Cl)Cl>[CH3:17][C:16]1[CH:15]=[CH:14][S:13][C:12]=1[C:10]1[C:9](=[O:18])[NH:8][C:7](=[O:19])[N:6]([CH2:5][CH2:4][CH2:3][CH:2]=[O:1])[CH:11]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 589942121-(4-Hydroxy-butyl)-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione

Product 1

HCID 58994229HCID 58994229, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Hydroxy-butyl)-5-(3-methyl-thiophen-2-yl)-1H-pyrimidine-2,4-dione (Prep 31, 30 mg, 0.11 mmol) was dissolved in dry DCM (2 mL), the solution was cooled to 0° C. and Dess-Martin periodinane (113 mg, 0.26 mmol) was added portionwise under nitrogen. The mixture was stirred at room temperature for 1.5 hours. Ethyl acetate was added and the solution washed with aqueous saturated Na2S2O3 (3 mL) and NaHCO3 (3 mL). The organic phase was dried (Na2SO4) and evaporated to give 30 mg of the title compound that was used in the next step without further purification (98% yield).

Workup

  1. washthe solution washed with aqueous saturated Na2S2O3 (3 mL) and NaHCO3 (3 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-baa49772bb874fcea3044e6892cedd97
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

Loading…