Lithium iodide → 79690-61-2

HRID 2296478Notes

Reaction equation

HRID 2296478 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:24])[CH:18]([CH3:23])[CH:19]([CH3:22])[CH2:20][CH3:21])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:25]([O:27]C)=[O:26].[I-].[Li+]>N1C=CC=CC=1>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:24])[CH:18]([CH3:23])[CH:19]([CH3:22])[CH2:20][CH3:21])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:25]([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 13060564HCID 13060564, compound

Product 1

HCID 13325979690-61-2Yield 30.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-oxo-10-(2,3-dimethylpentanamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (3.4 g) and anhydrous lithium iodide (8.5 g) in dry pyridine (34 ml) was stirred at 100° C. for 1 hour and 20 minutes. The reaction mixture was concentrated under reduced pressure. Water was added to the residue to give precipitates, which were collected by filtration and washed with water. The resulting crystals were suspended in water. The suspension was adjusted to pH 1-2 with conc. hydrochloric acid to give yellow crystals, which were separated by filtration, washed with water, and dried. The crude crystals (3.85 g) were dissolved in a mixture of chloroform and methanol under heating. The solution was filtered to remove insoluble materials. The filtrate was concentrated under reduced pressure to 40 ml and cooled in an ice bath. The resulting crystals were collected by filtration and suspended in a mixture of chloroform and methanol under heating. After the suspension was cooled to ambient temperature, the crystals were filtered and dried. There was obtained 4-oxo-10-(2,3-dimethylpentanamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (1.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. customto give
  4. customprecipitates
  5. filtrationwhich were collected by filtration
  6. washwashed with water
  7. customto give yellow crystals, which
  8. customwere separated by filtration
  9. washwashed with water
  10. customdried
  11. dissolutionThe crude crystals (3.85 g) were dissolved in a mixture of chloroform and methanol
  12. temperatureunder heating
  13. filtrationThe solution was filtered
  14. customto remove insoluble materials
  15. concentrationThe filtrate was concentrated under reduced pressure to 40 ml
  16. temperaturecooled in an ice bath
  17. filtrationThe resulting crystals were collected by filtration
  18. additionsuspended in a mixture of chloroform and methanol
  19. temperatureunder heating
  20. temperatureAfter the suspension was cooled to ambient temperature
  21. filtrationthe crystals were filtered
  22. customdried

Sources & evidence

ORD record
ord-739155693dde48d29e6efc0ebd9c04fd
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

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