Dimethylformamide → Dimethyl[[6-(2-ethylbutyramido)-4-quinazolinylamino]methylene]propanedioate

HRID 1719954Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:19])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.CO[CH:22]=[C:23]([C:28]([O:30][CH3:31])=[O:29])[C:24]([O:26][CH3:27])=[O:25].CN(C)C=O>O>[CH3:27][O:26][C:24](=[O:25])[C:23](=[CH:22][NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:19])[CH:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1)[C:28]([O:30][CH3:31])=[O:29]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-amino-6-(2-ethylbutyramido)-quinazoline (5.58 g), dimethyl methoxymethylenepropanedioate (5.62 g) and N,N-dimethylformamide (22 ml) was stirred at 100° C. for 1.5 hours. After cooling to ambient temperature, water (90 ml) was added to the reaction mixture. The resulting solid was separated by filtration, washed with water and dried to give dimethyl[[6-(2-ethylbutyramido)-4-quinazolinylamino]methylene]propanedioate (4.85 g).

Workup

temperatureAfter cooling to ambient temperature
customThe resulting solid was separated by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-40395b298bb54901846d5292396fb08b
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04543356

Reaction notes

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