Lithium iodide → HCID 67954680, compound

HRID 714421Notes

Reaction equation

HRID 714421 reaction equation
[O:1]=[C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:5][CH:4]=[C:3]1[C:20]([O:22]CC)=[O:21].[I-].[Li+]>N1C=CC=CC=1>[O:1]=[C:2]1[N:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)=[N:5][CH:4]=[C:3]1[C:20]([OH:22])=[O:21]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 67954353HCID 67954353, compound2×

Product 1

HCID 67954680HCID 67954680, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
127.5 °C

Procedure

A suspension of ethyl 1,6-dihydro-6-oxo-1-phenyl-2-(3-pyridinyl)-5-pyrimidinecarboxylate (i.e. the product from Example 7, Step B) (5.0 g, 15.5 mmol) and lithium iodide (powder, 5.2 g, 38.8 mmol) in pyridine (15 mL) was heated to 125-130° C. for 12 h. After cooling to ambient temperature, excess solvent was removed under reduced pressure. The resulting residue was dissolved in water (100 mL) and acidified with hydrochloric acid (6 N) to pH 7. The resulting dark brown solution was extracted with ethyl acetate (1×100 mL) to remove the non polar impurities. The aqueous layer was again extracted with dichloromethane/methanol (95:5) (2×50 mL). After initial extractions, the aqueous layer was slowly acidified to pH 4 and further extracted with dichloromethane/methanol (95:5) (3×50 mL). The combined neutral and acidic extracts were washed with brine and dried over anhydrous Na2SO4. The residue obtained after removal of the solvent was dried under high-vacuum to obtain 3.4 g of the title compound as a light brown solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customexcess solvent was removed under reduced pressure
  3. dissolutionThe resulting residue was dissolved in water (100 mL)
  4. extractionThe resulting dark brown solution was extracted with ethyl acetate (1×100 mL)
  5. customto remove the non polar impurities
  6. extractionThe aqueous layer was again extracted with dichloromethane/methanol (95:5) (2×50 mL)
  7. extractionAfter initial extractions
  8. extractionfurther extracted with dichloromethane/methanol (95:5) (3×50 mL)
  9. washThe combined neutral and acidic extracts were washed with brine
  10. dry with materialdried over anhydrous Na2SO4
  11. customThe residue obtained
  12. customafter removal of the solvent
  13. customwas dried under high-vacuum

Sources & evidence

ORD record
ord-4aa3c0e066a04571a2827d1d7590bbf9
Source dataset
uspto-grants-2015_11
Patent number
US09187432B2

Reaction notes

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