Water → HCID 13060567, compound

HRID 2296445Notes

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-b9a339add28746f9a389310b02cb685b
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04429126

Reaction notes

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