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

HRID 354877Notes

Reaction equation

HRID 354877 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:19])[CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C([O:22][CH:23]=[C:24]([C:30](OCC)=O)[C:25]([O:27][CH2:28][CH3:29])=[O:26])C.CN(C)C=O.O>C(OCC)(=O)C>[O:22]=[C:23]1[N:3]2[CH:4]=[N:5][C:6]3[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:19])[CH2:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[CH:10][C:11]=3[C:2]2=[N:1][CH:30]=[C:24]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 6871Diethyl (ethoxymethylene)malonateHCID 130604604-Amino-6-(3,3-dimethylbutyramido)quinazoline

Product 1

HCID 13060536ethyl 4-oxo-10-(3,3-dimethylbutanamido)-4H-pyrimido[1,2-c]quinazoline-3-carboxylateYield 26%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-amino-6-(3,3-dimethylbutyramido)quinazoline (12.2 g), diethyl ethoxymethylenepropandioate (15.3 g) and N,N-dimethylformamide (50 ml) was stirred at 150° C. for 2 hours. The reaction mixture was cooled to ambient temperature. After adding water, the resultant mixture was extracted with chloroform. The chloroform layer was washed twice with water and once with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a residue, to which was added ethyl acetate. Insoluble materials were separated by filtration and dried to give ethyl 4-oxo-10-(3,3-dimethylbutanamido)-4H-pyrimido[1,2-c]quinazoline-3-carboxylate (4.7 g) melting at 253°-254° C. Further, the filtrate was concentrated under reduced pressure to give a residue, which was recrystallized from a mixture of ethyl acetate and hexane to give crystalline diethyl [{6-(3,3-dimethylbutyramido)4-quinazolinylamino}methylene]propanedioate (10.1 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionthe resultant mixture was extracted with chloroform
  3. washThe chloroform layer was washed twice with water and once with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a residue
  7. customInsoluble materials were separated by filtration
  8. customdried

Sources & evidence

ORD record
ord-0ebe028b60d04f839c73882637fcaa71
Source dataset
uspto-grants-1983_03
Patent number
US04377580

Reaction notes

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