Potassium Hydroxide → HCID 15837480, compound

HRID 1871278Notes

Reaction equation

HRID 1871278 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]([C:15]([O:28][CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13]C)=[O:12])[CH:6]=[C:5]([O:30][CH3:31])[N:4]=1.[OH-].[K+]>O1CCOCC1.O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH:10]([C:15]([O:28][CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([OH:13])=[O:12])[CH:6]=[C:5]([O:30][CH3:31])[N:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 15837479HCID 15837479, compound

Product 1

HCID 15837480HCID 15837480, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

550 mg (1.3 mmol) of methyl 2-(2,6-dimethoxy-4-pyrimidinyl-oxy)-3-methoxy-3,3-diphenylpropionate were dissolved in 5 ml of dioxane, 2.6 ml of 1N KOH solution were added, and the mixture was stirred at 100° C. for 3 h. The solution was diluted with 300 ml of water and extracted with ethyl acetate to remove unreacted ester. The aqueous phase was then adjusted to pH 1-2 with dilute hydrochloric acid and was extracted with ethyl acetate. After drying over magnesium sulfate and removal of the solvent by distillation, the residual foam (425 mg) was purified by MPLC, resulting in 205 mg (40%) of product as foam.

Workup

  1. extractionextracted with ethyl acetate
  2. customto remove unreacted ester
  3. extractionwas extracted with ethyl acetate
  4. dry with materialAfter drying over magnesium sulfate and removal of the solvent by distillation
  5. customthe residual foam (425 mg) was purified by MPLC

Sources & evidence

ORD record
ord-5a85611c309b493281935837a14cc953
Source dataset
uspto-grants-2000_08
Patent number
US06103732

Reaction notes

Loading…