Diphenyl Ether → HCID 13060552, compound

HRID 2296459Notes

Reaction equation

HRID 2296459 reaction equation
[C:1]([NH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[C:11]2[NH:18][CH:19]=[C:20]([C:25]([O:27]C)=O)[C:21]([O:23][CH3:24])=[O:22])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[O:27]=[C:25]1[N:12]2[CH:13]=[N:14][C:15]3[CH:16]=[CH:17][C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4])=[CH:9][C:10]=3[C:11]2=[N:18][CH:19]=[C:20]1[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 13060511HCID 13060511, compound

Product 1

HCID 13060552HCID 13060552, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
260 °C

Procedure

A mixture of dimethyl [{6-pivalamido-4-quinazolinylamino}methylene]propanedioate (24.5 g) and diphenyl ether (150 ml) was heated at 260° C. for 20 minutes and cooled to ambient temperature. To the reaction mixture was added hexane to give crystals, which were filtered off, washed with hexane and dissolved in chloroform (400 ml) under heating. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to 200 ml and allowed to stand under cooling. The precipitated crystals were filtered off and washed with chloroform to give crystalline methyl 4-oxo-10-pivalamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylate (18.29 g). The mother liquor was concentrated under reduced pressure to give crystals, which are purified by a column chromatography on silica gel (50 g) (Developing solvent: 5% methanol-chloroform solution) and recrystallized from chloroform to give the same object compound (3.2 g).

Workup

  1. temperaturecooled to ambient temperature
  2. customto give crystals, which
  3. filtrationwere filtered off
  4. washwashed with hexane
  5. dissolutiondissolved in chloroform (400 ml)
  6. temperatureunder heating
  7. customInsoluble materials were removed by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure to 200 ml
  9. temperatureunder cooling
  10. filtrationThe precipitated crystals were filtered off
  11. washwashed with chloroform

Sources & evidence

ORD record
ord-78fedea17b654a92bc40b9b4f98f6b98
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

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