Lithium iodide → HCID 67954838, compound

HRID 1846386Notes

Reaction equation

HRID 1846386 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:5][CH:4]=[C:3]1[C:21]([O:23]CC)=[O:22].[I-].[Li+]>N1C=CC=CC=1>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:5][CH:4]=[C:3]1[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 67954621HCID 67954621, compound2×

Product 1

HCID 67954838HCID 67954838, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of ethyl 1,6-dihydro-6-oxo-2-phenyl-1-(phenylmethyl)-5-pyrimidinecarboxylate (i.e. the product from Step B) (2.9 g, 8.6 mmol) in pyridine (15 mL) was added lithium iodide (3.01 g, 21.7 mmol). The reaction mixture was heated to reflux for 4 h, cooled, and then stirred at room temperature for 72 h. The reaction mixture was concentrated under reduced pressure. To the resulting residue was added water (10 mL), followed by 1 N hydrochloric acid until the pH was 7. The solution was filtered through Celite® diatomaceous filter aid, and the filtrate was acidified with 1 N hydrochloric acid until the pH was 1. The mixture was extracted with dichloromethane, and the organic layer was dried (MgSO4) and concentrated under reduced pressure to afford a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a white solid (2.2 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 h
  3. temperaturecooled
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionTo the resulting residue was added water (10 mL)
  6. filtrationThe solution was filtered through Celite® diatomaceous filter aid
  7. extractionThe mixture was extracted with dichloromethane
  8. dry with materialthe organic layer was dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customto afford a solid, which
  11. washwas washed with diethyl ether
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-c65431d7258b46d2addb49ca3b9a7435
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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