Water → ethyl 4-oxo-10-methanesulfonamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylate

HRID 354878Notes

Reaction equation

HRID 354878 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C([O:19][CH:20]=[C:21]([C:27](OCC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])C.CN(C)C=O.O>C(Cl)(Cl)Cl>[O:19]=[C:20]1[N:3]2[CH:4]=[N:5][C:6]3[CH:7]=[CH:8][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:10][C:11]=3[C:2]2=[N:1][CH:27]=[C:21]1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6871Diethyl (ethoxymethylene)malonate2×HCID 130604594-Amino-6-methanesulfonamidoquinazoline

Product 1

HCID 13060551ethyl 4-oxo-10-methanesulfonamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylateYield 3.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-amino-6-methanesulfonamidoquinazoline (2.0 g), diethyl ethoxymethylenepropanedioate (3.15 g) and N,N-dimethylformamide (16 ml) was stirred at 140° C. for an hour and a half. To the reaction mixture was added diethyl ethoxymethylenepropanedioate (1.57 g). The reaction mixture was stirred for an hour and cooled to ambient temperature. To the mixture was added water to five crystals, which were filtered off and dissolved in a mixture of chloroform and methanol. The solution was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue, to which was added chloroform. The mixture was heated and insoluble materials were filtered off to give crystalline ethyl 4-oxo-10-methanesulfonamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylate (0.12 g) melting at 310°-312° C. Further, the filtrate was concentrated under reduced pressure and allowed to stand at ambient temperature to give crystals (1.63 g), which were purified by a column chromatography on silica gel (60 g) (developing solvent: 3% methanol-chloroform solution). The crystals were dissolved in 10% methanol-chloroform solution. The solution was treated with activated charcoal and concentrated under reduced pressure. The residue was recrystallized from chloroform to give crystalline diethyl [{6-methanesulfonamido-4-quinazolinylamino}methylene]propanedioate (1.45 g).

Workup

  1. stirringThe reaction mixture was stirred for an hour
  2. temperaturecooled to ambient temperature
  3. filtrationwere filtered off
  4. dissolutiondissolved in a mixture of chloroform and methanol
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue
  8. temperatureThe mixture was heated
  9. filtrationinsoluble materials were filtered off

Sources & evidence

ORD record
ord-6f473d1c4927494fa961a4dd32a76ac5
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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