Hexane → HCID 13060565, compound

HRID 354903Notes

Reaction equation

HRID 354903 reaction equation
[C:1]([NH:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([NH:18][CH:19]=[C:20]([C:25]([O:27]C)=O)[C:21]([O:23][CH3:24])=[O:22])=[N:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[O:27]=[C:25]1[N:13]2[CH:14]=[N:15][C:16]3[CH:17]=[C:8]([NH:7][C:1](=[O:6])[C:2]([CH3:4])([CH3:5])[CH3:3])[CH:9]=[CH:10][C:11]=3[C:12]2=[N:18][CH:19]=[C:20]1[C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 8058HexaneHCID 13060509HCID 13060509, compound

Product 1

HCID 13060565HCID 13060565, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
250 °C

Procedure

A mixture of dimethyl [[7-pivalamido-4-quinazolinylamino]methylene]propanedioate (11.7 g) in diphenyl ether (58 ml) was stirred at 250° C. for 15 minutes and cooled to ambient temperature. Hexane was added to the reaction mixture. The resulting crystals were collected by filtration, washed with hexane, and dried. The crystals were dissolved in a mixture of chloroform and ethanol under heating. The solution was filtered to remove insoluble materials. The filtrate was concentrated under reduced pressure until crystallization began. After the solution was cooled to ambient temperature, the resulting crystals were collected by filtration to give methyl 4-oxo-9-pivalamido-4H-pirimido[1,2-C]quinazoline-3-carboxylate (5.1 g). Concentration of the mother liquor gave additional crystals of the same compound (3.4 g).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe resulting crystals were collected by filtration
  3. washwashed with hexane
  4. customdried
  5. dissolutionThe crystals were dissolved in a mixture of chloroform and ethanol
  6. temperatureunder heating
  7. filtrationThe solution was filtered
  8. customto remove insoluble materials
  9. concentrationThe filtrate was concentrated under reduced pressure until crystallization
  10. temperatureAfter the solution was cooled to ambient temperature
  11. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-357beb4735034d8aa2e0b72a660b8bc3
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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