Lithium iodide → HCID 67954869, compound

HRID 714431Notes

Reaction equation

HRID 714431 reaction equation
[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][N:9]=[C:8]2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[Li+]>C(OCC)(=O)C>[CH:1]1([N:7]2[C:12](=[O:13])[C:11]([C:14]([OH:16])=[O:15])=[CH:10][N:9]=[C:8]2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 67954671HCID 67954671, compound2×

Product 1

HCID 67954869HCID 67954869, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 1-cyclohexyl-1,6-dihydro-6-oxo-2-phenyl-5-pyrimidinecarboxyate (1.41 g, 4.32 mmol) (i.e. the product from Example 11, Step A) was dissolved in ethyl acetate and treated with lithium iodide (powder, 1.72 g, 12.8 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate was added and the resulting solution was extracted with ethyl acetate which was then discarded. The aqueous layer was made acidic with hydrochloric acid (1 N) and then extracted with dichloromethane (2×40 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure resulting in 0.58 g of the title product as a solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customThe crude reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. additionaqueous sodium bicarbonate was added
  6. extractionthe resulting solution was extracted with ethyl acetate which
  7. extractionextracted with dichloromethane (2×40 mL)
  8. dry with materialThe combined organic extracts were dried over MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-67fa85a86e9e42a7915364c9184cd9d1
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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