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

HRID 2296465

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 are 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
customare recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record: ord-21e053ac7b86401fa9bcb263c05ae783
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04429126

Linked notes

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