4-Aminoquinazoline → Dimethyl [(4-quinazolinylamino)methylene]propanedioate

HRID 354866

Reaction equation

HRID 354866 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.CO[CH:14]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17]>CN(C)C=O>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([NH:1][CH:14]=[C:15]([C:20]([O:22][CH3:23])=[O:21])[C:16]([O:18][CH3:19])=[O:17])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 847594-AminoquinazolineHCID 90770Dimethyl methoxymethylenemalonate

Product 1

HCID 86738820Dimethyl [(4-quinazolinylamino)methylene]propanedioateYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-aminoquinazoline (7.27 g) and dimethyl methoxymethylenepropanedioate (9.6 g) in N,N-dimethylformamide (35 ml) was stirred for 2 hours at 150° C. The reaction mixture was cooled to ambient temperature and poured into ice-water to give crystals, which were separated by filtration, washed with water and dried to ambient temperature to give a mixture (13.3 g) of dimethyl [(4-quinazolinylamino)methylene]propanedioate and methyl 4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylate.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customto give crystals, which
  3. customwere separated by filtration
  4. washwashed with water
  5. customdried to ambient temperature

Sources & evidence

ORD record
ord-d4a58274e2c24f558519a627f1b5b1e5
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Linked notes

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