Hydrochloric Acid → HCID 13060566, compound

HRID 354904Notes

Reaction equation

HRID 354904 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:23]([O:25]C)=[O:24].[I-].[Li+].Cl>N1C=CC=CC=1.O>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:22])[C:18]([CH3:20])([CH3:21])[CH3:19])[CH:13]=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:23]([OH:25])=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66321Lithium iodideHCID 13060565HCID 13060565, compound

Product 1

HCID 13060566HCID 13060566, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-oxo-9-pivalamido-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (6.5 g) and anhydrous lithium iodide (16.25 g) in dry pyridine (65 ml) was stirred at 100° C. for 1 hour and 30 minutes and at 120° C. for additional 30 minutes. The reaction mixture was concentrated under reduced pressure to give an oily residue, which was dissolved in water. The resulting solution was adjusted to pH 1 with conc. hydrochloric acid to give yellow crystals, which were separated by filtration, washed with water, and dried. The crude crystals were dissolved in a mixture of chloroform and methanol under heating. The solution was filtered to remove insoluble materials. The solution was concentrated under reduced pressure until crystallization began and cooled. The resulting crystals were collected by filtration and dried. There was obtained 4-oxo-9-pivalamido-4H-pyrimido-[1,2-C]quinazoline-3-carboxylic acid (2.9 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give an oily residue, which
  3. customto give yellow crystals, which
  4. customwere separated by filtration
  5. washwashed with water
  6. customdried
  7. dissolutionThe crude crystals were dissolved in a mixture of chloroform and methanol
  8. temperatureunder heating
  9. filtrationThe solution was filtered
  10. customto remove insoluble materials
  11. concentrationThe solution was concentrated under reduced pressure until crystallization
  12. temperaturecooled
  13. filtrationThe resulting crystals were collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-cc49c9ade93e4832a49fd3578548e689
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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