Hexane → 4H-pyrimido[1,2-c]quinazoline-4-one

HRID 354874Notes

Reaction equation

HRID 354874 reaction equation
CC1(C)OC(=O)[C:5](=[CH:9][NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:4](=O)[O:3]1.CCCCCC.C(OCC)(=O)C>C1(OC2C=CC=CC=2)C=CC=CC=1>[N:10]1[CH:9]=[CH:5][C:4](=[O:3])[N:12]2[C:11]=1[C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:14]=[CH:13]2

Participants

5

Reactant 3

HCID 8058Hexane2×HCID 8857Ethyl AcetateHCID 130605182,2-Dimethyl-5-[(4-quinazolinyl)amino]methylene-1,3-dioxane-4,6-dione

Product 1

HCID 130605704H-pyrimido[1,2-c]quinazoline-4-oneYield 69.4%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A mixture of 2,2-dimethyl-5-[(4-quinazolinyl)amino]methylene-1,3-dioxane-4,6-dione (3.5 g) in diphenylether (15 ml) was stirred for 10 minutes at 250°-260° C. and then cooled to ambient temperature. To the reaction mixture was added hexane and allowed to to stand at ambient temperature to give crystals, which were separated by filtration and washed with hexane to give crude crystals (3 g). The crude crystals were subjected to a column chromatography using silica gel (developing solvent: a mixture of ethyl acetate and hexane (3:7)). The eluate was concentrated under reduced pressure to give crystals, which were recrystallized from chloroform and hexane to give 4H-pyrimido[1,2-c]quinazoline-4-one (1.6 g).

Workup

  1. customto to stand at ambient temperature
  2. customto give crystals, which
  3. customwere separated by filtration
  4. washwashed with hexane
  5. customto give crude crystals (3 g)
  6. concentrationThe eluate was concentrated under reduced pressure
  7. customto give crystals, which
  8. customwere recrystallized from chloroform and hexane

Sources & evidence

ORD record
ord-da56535d6c40405bb8c1363e0f6181e7
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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