Water → Diethyl [[6-(2-ethylbutyramido)-4-quinazolinylamino]methylene]propanedioate

HRID 1719965Notes

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.C(O[CH:23]=[C:24]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])C.O>CN(C)C=O>[CH2:15]([CH:14]([CH2:17][CH3:18])[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:23]=[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:19])[CH3:16]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-amino-6-(2-ethylbutyramido)-quinazoline (0.9 g) and diethyl ethoxymethylenepropanedioate (0.95 g) in N,N-dimethylformamide (4 ml) was stirred at 100° C. for 2 hours and 40 minutes. Water was added to the reaction mixture. The resulting crystals were collected, washed with water and dried. The crude crystals were chromatographed on silica gel with 20% ethyl acetate-chloroform and recrystallized from a mixture of ethyl acetate, chloroform and hexane to give crystalline diethyl [[6-(2-ethylbutyramido)-4-quinazolinylamino]methylene]propanedioate (1.1 g).

Workup

customThe resulting crystals were collected
washwashed with water
customdried
customThe crude crystals were chromatographed on silica gel with 20% ethyl acetate-chloroform
customrecrystallized from a mixture of ethyl acetate, chloroform and hexane

Sources & evidence

ORD record: ord-7da07ea2dfe048e3acb2d300216efd35
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04543356

Reaction notes

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