Dimethylformamide → Dimethyl[{6-(3,3-dimethylbutyramido)-4-quinazolinylamino}methylene]propanedioate

HRID 354876Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-amino-6-(3,3-dimethylbutyramido)quinazoline (8.5 g), dimethyl methoxymethylenepropanedioate (12.75 g) and N,N-dimethylformamide (34 g) was stirred for an hour at 100° C. After cooling to ambient temperature, to the resultant mixture was added water to give precipitates, which were separated by filtration, washed with water and dried to give crystalline dimethyl [{6-(3,3-dimethylbutyramido)-4-quinazolinylamino}methylene]propanedioate (10.9 g).

Workup

customto give
customprecipitates
customwhich were separated by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-6f04d01d001e42d49a57e812aa48595c
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04377580

Reaction notes

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