Water → HCID 13060567, compound

HRID 354867Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:13])=[C:9]([CH3:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C.O>CN(C)C=O.CO.C(Cl)(Cl)Cl>[CH3:13][C:8]1[C:9]([CH3:12])=[CH:10][C:11]2[C:2]3[N:3]([C:17](=[O:16])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24][N:1]=3)[CH:4]=[N:5][C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-amino-6,7-dimethylquinazoline (11.3 g) and diethyl ethoxymethylenepropanedioate (15.55 g) in N,N-dimethylformamide (45 ml) was stirred for 4 hours at 110° C. After the reaction mixture was cooled to ambient temperature, to the mixture was added water to give crystals, which were separated by filtration, washed with water and dried under reduced pressure to give crude crystals (18.5 g). The crude crustals were dissolved in 1% methanol-chloroform solution (500 ml) and concentrated under reduced pressure after insoluble materials were removed by filtration. The residue was recrystallized from chloroform to give crystalline ethyl 9,10-dimethyl-4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylate (3.57 g).

Workup

temperatureAfter the reaction mixture was cooled to ambient temperature, to the mixture
customto give crystals, which
customwere separated by filtration
washwashed with water
customdried under reduced pressure
customto give crude crystals (18.5 g)
concentrationconcentrated under reduced pressure after insoluble materials
customwere removed by filtration
customThe residue was recrystallized from chloroform

Sources & evidence

ORD record: ord-95ccd14415184ecd9738dc45081aab77
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04377580

Reaction notes

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