Dimethyl[[6-(2-methylpropionamido)-4-quinazolinylamino]methylene]propanedioate → methyl 4-oxo-10-(2-methylpropionamido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate
Reaction equation
[CH3:1][CH:2]([CH3:27])[C:3]([NH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:16][CH:17]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:19]([O:21]C)=O)=[O:4]>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)Cl.CO>[O:21]=[C:19]1[N:10]2[CH:11]=[N:12][C:13]3[CH:14]=[CH:15][C:6]([NH:5][C:3](=[O:4])[CH:2]([CH3:1])[CH3:27])=[CH:7][C:8]=3[C:9]2=[N:16][CH:17]=[C:18]1[C:23]([O:25][CH3:26])=[O:24]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
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 reduce pressure to about 150 ml. After cooling, there was obtained crystalline methyl 4-oxo-10-(2-methyl-propionamido)-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
- temperatureAfter cooling
Sources & evidence
- ORD record
- ord-58327142d9d04b938c2ec6fb7e7e1c70
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377580
Reaction notes
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