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

HRID 354879
Notes
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Reaction equation

HRID 354879 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>[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6871Diethyl (ethoxymethylene)malonateHCID 130604594-Amino-6-methanesulfonamidoquinazoline

Product 1

HCID 13060551ethyl 4-oxo-10-methanesulfonamido-4H-pyrimido[1,2-c]quinazoline-3-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 4-amino-6-methanesulfonamidoquinazoline (6.89 g), diethyl ethoxymethylenepropanediate (15.5 g) and N,N-dimethylformamide (55 ml) was stirred at 155° C. for 2.5 hours. The reaction mixture was cooled to ambient temperature. To the mixture was added water to give precipitates, which were separated by filtration and washed with water. To the crystals was added a mixture of methanol and chloroform (1:4) (400 ml). After stirring under heating, insoluble materials (6.95 g) were filtered off and recrystallized from N,N-dimethylformamide to give crystalline ethyl 4-oxo-10-methanesulfonamido-4H-pyrimido [1,2-c]quinazoline-3-carboxylate (5.76 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customto give
  3. customprecipitates
  4. customwhich were separated by filtration
  5. washwashed with water
  6. additionTo the crystals was added
  7. additiona mixture of methanol and chloroform (1:4) (400 ml)
  8. stirringAfter stirring
  9. temperatureunder heating
  10. filtrationinsoluble materials (6.95 g) were filtered off
  11. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-d17d56ac5664455c83b696d91517012c
Source dataset
uspto-grants-1983_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04377580

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes