Lithium iodide → 1,6-Dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid

HRID 714428Notes

Reaction equation

HRID 714428 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]([C:12]([O:14]CC)=[O:13])=[CH:8][N:7]=[C:6]1[C:17]1[CH:21]=[CH:20][S:19][CH:18]=1.[I-].[Li+]>C(OCC)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:10](=[O:11])[C:9]([C:12]([OH:14])=[O:13])=[CH:8][N:7]=[C:6]1[C:17]1[CH:21]=[CH:20][S:19][CH:18]=1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 67954683Ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate2×

Product 1

HCID 679551311,6-Dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 1,6-dihydro-1-(2-methoxyethyl)-6-oxo-2-(3-thienyl)-5-pyrimidinecarboxylate a (1.82 g, 5.90 mmol) (i.e. the product from Example 10, Step B) was dissolved in ethyl acetate and treated with lithium iodide (powder, 2.36 g, 17.6 mmol) and heated to reflux for 16 h. The crude reaction mixture was concentrated under reduced pressure and then aqueous sodium bicarbonate solution 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 organics were dried over MgSO4 and concentrated under reduced pressure to provide the title compound 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 solution was added
  6. extractionthe resulting solution was extracted with ethyl acetate which
  7. extractionextracted with dichloromethane (2×40 mL)
  8. dry with materialThe combined organics were dried over MgSO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-649aacd7c8e5423fb0728ca361c20bd4
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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