Lithium iodide → HCID 13060561, compound

HRID 354894Notes

Reaction equation

HRID 354894 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]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[O:18])=[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]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[O:18])=[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 13060557HCID 13060557, compound

Product 1

HCID 13060561HCID 13060561, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-oxo-10-cyclohexanecarboxamido-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (4.7 g) and anhydrous lithium iodide (11.75 g) in dry pyridine (47 ml) was stirred at 100° C. for 1 hour and 20 minutes and cooled to ambient temperature. The resulting solid was collected by filtration and washed with ethanol. The solid was suspended in water (100 ml). 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 were washed with a mixture of chloroform and methanol and dried. There was obtained 4-oxo-10-cyclohexanecarboxamido-4H-pyrimido[1,2-C]quinazoline-3-carboxylic acid (2.75 g).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with ethanol
  4. customto give yellow crystals which
  5. customwere separated by filtration
  6. washwashed with water
  7. customdried
  8. washThe crude crystals were washed with a mixture of chloroform and methanol
  9. customdried

Sources & evidence

ORD record
ord-528af3dea644403d944d1558f622186b
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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