Diethyl (ethoxymethylene)malonate → HCID 13060483, compound

HRID 1719932Notes

Reaction equation

HRID 1719932 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(O[CH:22]=[C:23]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])C>C(O)C(C)C>[CH2:27]([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]([N:12]3[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]3)[CH:10]=2)[N:5]=[CH:4][N:3]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH3:28]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 13060450HCID 13060450, compound

Product 1

HCID 13060483HCID 13060483, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-6-(4-methylpiperazinyl)quinazoline (2.19 g) and diethyl ethoxymethylenepropanedioate (2.13 g) in isobutylalcohol (9 ml) was stirred for 2 hours and 25 minutes at 100° C. and then cooled to ambient temperature. The resultant mixture was concentrated under reduced pressure to give a residue, which was recrystallized from ethanol to give crystalline diethyl[{6-(4-methylpiperazinyl)-4-quinazolinylamino}methylene]propanedioate (1.58 g).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationThe resultant mixture was concentrated under reduced pressure
  3. customto give a residue, which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-b8cc39b178984bfe92c7e52c31b1c637
Source dataset
uspto-grants-1985_09
Patent number
US04543356

Reaction notes

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