Dimethyl[[6-(2-methylpropionamido)-4-quinazolinylamino]methylene]propanedioate → methyl 4-oxo-10-(2-methylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate

HRID 1719958Notes

Reaction equation

C[O:2][C:3](=O)[C:4](=[CH:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[CH:19]=2)[N:14]=[CH:13][N:12]=1)[C:5]([O:7][CH3:8])=[O:6]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)Cl.CO>[O:2]=[C:3]1[N:12]2[CH:13]=[N:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[CH:19][C:20]=3[C:11]2=[N:10][CH:9]=[C:4]1[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 255 °C

Procedure

A mixture of dimethyl[[6-(2-methylpropionamido)-4-quinazolinylamino]methylene]propanedioate (8.4 g) in diphenyl ether (42 ml) was stirred at 255° C. for 15 minutes. The reaction mixture was cooled to ambient temperature to give crystals which were filtered off, washed with hexane and dried. There were obtained 6.9 g of the crude crystals. The crude crystals were dissolved in a mixture of chloroform and methanol (4:1) under heating. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to about 150 ml. After cooling, there was obtained crystalline methyl 4-oxo-10-(2-methylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (5.85 g).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customto give crystals which
filtrationwere filtered off
washwashed with hexane
customdried
customThere were obtained 6.9 g of the crude crystals
temperatureunder heating
customInsoluble materials were removed by filtration
concentrationThe filtrate was concentrated under reduced pressure to about 150 ml
temperatureAfter cooling

Sources & evidence

ORD record: ord-4528ac3afb68479e8337cfda3db4d5f1
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04543356

Reaction notes

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