Water → HCID 131712977, compound

HRID 354864

Reaction equation

HRID 354864 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[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.O>CN(C)C=O>[Cl: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:16]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 6871Diethyl (ethoxymethylene)malonateHCID 3202476-Chloroquinazolin-4-amine

Product 1

HCID 131712977HCID 131712977, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-amino-6-chloroquinazoline (8.7 g) and diethyl ethoxymethylenepropanedioate (11.53 g) in N,N-dimethylformamide (25 ml) was stirred for 2 hours and 40 minutes at 150° C. After the reaction mixture was cooled to ambient temperature, to the mixture was added water with stirring to give crystals, which were washed with water, dried under reduced pressure and dissolved in ethyl acetate under heating. Insoluble materials were filtered off. To the filtrate was added hexane and allowed to stand at ambient temperature to give crystals, which were separated by filtration and washed with a mixture of ethyl acetate and hexane to give a mixture (13.48 g) of crystalline diethyl [(6-chloro-4-quinazolinylamino)methylene]propanedioate and ethyl 10-chloro-4-oxo-4H-pyrimido[1,2-c]quinazoline-3-carboxylate.

Workup

  1. temperatureAfter the reaction mixture was cooled to ambient temperature, to the mixture
  2. stirringwith stirring
  3. customto give crystals, which
  4. washwere washed with water
  5. customdried under reduced pressure
  6. dissolutiondissolved in ethyl acetate
  7. temperatureunder heating
  8. filtrationInsoluble materials were filtered off
  9. additionTo the filtrate was added hexane
  10. customto stand at ambient temperature
  11. customto give crystals, which
  12. customwere separated by filtration
  13. washwashed with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-50c351ae4dee4619a8f86ea16cc4338e
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Linked notes

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