Diphenyl Ether → ethyl 4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylate

HRID 354873Notes

Reaction equation

HRID 354873 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14](OCC)=[O:15])=[N:3][CH:2]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[O:15]=[C:14]1[N:3]2[CH:2]=[N:1][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[C:4]2=[N:11][CH:12]=[C:13]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 13060467Diethyl[(4-quinazolinylamino)methylene]propanedioate

Product 1

HCID 13060520ethyl 4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylateYield 90.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
250 °C

Procedure

To diethyl [(4-quinazolinylamino)methylene]propanedioate (16.0 g) was added diphenylether (70 ml) which had been heated at 250° C. in advance. The reaction mixture was stirred at 250°-260° C. for 20 minutes and cooled to ambient temperature. To the resultant mixture was added hexane. The mixture was stirred to give crystals, which was washed with hexane and dried. The crude crystals were dissolved in ethyl acetate under heating. After insoluble materials were removed by filtration, the filtrate was concentrated under reduced pressure to a volume of 200 ml. To the concentrate was added hexane and the mixture was allowed to stand at ambient temperature to precipitate crystals, which were separated by filtration, washed with a mixture of ethyl acetate and hexane and dried to give crystalline ethyl 4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylate (12.4 g).

Workup

  1. temperaturecooled to ambient temperature
  2. stirringThe mixture was stirred
  3. customto give crystals, which
  4. washwas washed with hexane
  5. customdried
  6. dissolutionThe crude crystals were dissolved in ethyl acetate
  7. temperatureunder heating
  8. customAfter insoluble materials were removed by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure to a volume of 200 ml
  10. additionTo the concentrate was added hexane
  11. customto stand at ambient temperature
  12. customto precipitate crystals, which
  13. customwere separated by filtration
  14. washwashed with a mixture of ethyl acetate and hexane
  15. customdried

Sources & evidence

ORD record
ord-35b77e846d5748fc9ecca1a426293fb9
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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