Diphenyl Ether → methyl 4-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate

HRID 354888

Reaction equation

[CH3:1][O:2][C:3](=[O:29])[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:28])[CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH:19]=2)[N:14]=[CH:13][N:12]=1)[C:5](OC)=[O:6].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[O:6]=[C:5]1[N:12]2[CH:13]=[N:14][C:15]3[CH:16]=[CH:17][C:18]([NH:21][C:22](=[O:28])[CH:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:19][C:20]=3[C:11]2=[N:10][CH:9]=[C:4]1[C:3]([O:2][CH3:1])=[O:29]

Participants

Conditions

Temperature: 255 °C

Procedure

A mixture of dimethyl[[6-(2-ethylbutyramido)-4-quinazolinylamino]methylene]propanedioate (5.3 g) and diphenyl ether (32 ml) was heated at 255° C. for 15 minutes and cooled to ambient temperature. Hexane was added to the reaction mixture. The resulting crystals were filtered off, washed with hexane and dried. The crude crystals were dissolved in a mixture of chloroform and methanol (10:1) under heating. Insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure to give crystals, which were recrystallized from a mixture of chloroform and hexane to give methyl 4-oxo-10-(2-ethylbutyramido)-4H-pyrimido[1,2-C]quinazoline-3-carboxylate (3.81 g).

Workup

temperaturecooled to ambient temperature
filtrationThe resulting crystals were filtered off
washwashed with hexane
customdried
dissolutionThe crude crystals were dissolved in a mixture of chloroform and methanol (10:1)
temperatureunder heating
customInsoluble materials were removed by filtration
concentrationThe filtrate was concentrated under reduced pressure
customto give crystals, which
customwere recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record: ord-c2457fe689d94c68b6796249a04d2da1
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04377580

Linked notes

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