Water → HCID 13060508, compound

HRID 354899Notes

Reaction equation

HRID 354899 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:20])[CH:14]([CH3:19])[CH:15]([CH3:18])[CH2:16][CH3:17])[CH:10]=2)[N:5]=[CH:4][N:3]=1.CO[CH:23]=[C:24]([C:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26].O>CN(C)C=O>[CH3:19][CH:14]([CH:15]([CH3:18])[CH2:16][CH3:17])[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:29]([O:31][CH3:32])=[O:30])[C:25]([O:27][CH3:28])=[O:26])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 90770Dimethyl methoxymethylenemalonateHCID 13060466HCID 13060466, compound

Product 1

HCID 13060508HCID 13060508, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-6-(2,3-dimethylpentanamido)quinazoline (6.75 g) and dimethyl methoxymethylenepropanedioate (6.48 g) in N,N-dimethylformamide (20 ml) was stirred at 100° C. for 1 hour and cooled to ambient temperature. Water was added to the reaction mixture. The resulting solid was separated by filtration, washed with water, and dried. There was obtained dimethyl [[6-(2,3-dimethylpentanamido)-4-quinazolinylamino]methylene]propanedioate (6.58 g). A portion of the crude product was chromatographed on silica gel with chloroform and ethyl acetate (3:1) and recrystallized from ethyl acetate to give analytically pure dimethyl [[6-(2,3-dimethylpentanamido)-4-quinazolinylamino]methylene]propanedioate (0.45 g).

Workup

  1. temperaturecooled to ambient temperature
  2. customThe resulting solid was separated by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-51477ac71d144ab2af8e8d8494cbb8da
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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