Diethyl (ethoxymethylene)malonate → HCID 86738819, compound

HRID 354865Notes

Reaction equation

HRID 354865 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>CN(C)C=O>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:1][CH:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 218256974-AMino-7-chloroquinazoline

Product 1

HCID 86738819HCID 86738819, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-amino-7-chloroquinazoline (1.3 g) and diethyl ethoxymethylenepropanedioate (1.72 g) in N,N-dimethylformamide (6 ml) was stirred for 2 hours at 150° C. The resultant mixture was cooled to ambient temperature and poured into ice-water to give crystals, which were separated by filtration, washed with water and recrystallized from ethanol to give a mixture (1.65 g) of diethyl [(7-chloro-4-quinazolinylamino)methylene]propanedioate and ethyl 9-chloro-4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylate. The mixture was subjected to a column chromatography using silica gel (developing solvent: a mixture of benzene and ethyl acetate (10:1)) to give purified crystals.

Workup

  1. customto give crystals, which
  2. customwere separated by filtration
  3. washwashed with water
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7f65673a2df443029331454d26d5661c
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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