Pyridine → HCID 13060573, compound

HRID 354884Notes

Reaction equation

HRID 354884 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][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:21]([O:23]C)=[O:22].[I-].[Li+].N1C=CC=CC=1>O>[O:1]=[C:2]1[N:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:14][C:15]=3[C:6]2=[N:5][CH:4]=[C:3]1[C:21]([OH:23])=[O:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 13060553HCID 13060553, compound

Product 1

HCID 13060573HCID 13060573, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-oxo-10-methanesulfonamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylate (4.32 g), anhydrous lithium iodide (10.8 g) and dry pyridine (43 ml) was stirred at 120° C. for 2 hours. The reaction mixture was concentrated under reduced pressure to give a residue, which was dissolved in water (900 ml). Insoluble materials were removed by filtration. The aqueous layer was adjusted to pH 5 with conc. hydrochloric acid to give crystals, which were filtered off, suspended in a mixture of chloroform and methanol, stirred and filtered to give crystals, which were dried to give crystalline 4-oxo-10-methanesulfonamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylic acid (2.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto give a residue, which
  3. customInsoluble materials were removed by filtration
  4. customto give crystals, which
  5. filtrationwere filtered off
  6. additionsuspended in a mixture of chloroform and methanol
  7. stirringstirred
  8. filtrationfiltered
  9. customto give crystals, which
  10. customwere dried

Sources & evidence

ORD record
ord-be0a5bbc50b34a1a95de04dda7e7fb22
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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