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Triethylamine → 1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]-piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione

HRID 1196717
Notes
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Reaction equation

HRID 1196717 reaction equation
C1(C2OC3C=C(OCCBr)C=CC=3C(=O)C=2)C=CC=CC=1.CN1C(N2CCNCC2)=CC(=O)N(C)C1=O.C(N(CC)CC)C.C(O)(=O)C(O)=O.[CH3:51][N:52]1[C:57]([N:58]2[CH2:63][CH2:62][N:61]([CH2:64][CH2:65][O:66][C:67]3[CH:83]=[CH:82][C:70]4[C:71](=[O:81])[CH:72]=[C:73]([C:75]5[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=5)[O:74][C:69]=4[CH:68]=3)[CH2:60][CH2:59]2)=[CH:56][C:55](=[O:84])[N:54]([CH3:85])[C:53]1=[O:86]>CN(C)C=O>[CH3:51][N:52]1[C:57]([N:58]2[CH2:59][CH2:60][N:61]([CH2:64][CH2:65][O:66][C:67]3[CH:83]=[CH:82][C:70]4[C:71](=[O:81])[CH:72]=[C:73]([C:75]5[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=5)[O:74][C:69]=4[CH:68]=3)[CH2:62][CH2:63]2)=[CH:56][C:55](=[O:84])[N:54]([CH3:85])[C:53]1=[O:86]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 198987461,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]piperazine-1-yl)-2,4-(1H,3H)-pyrimidinedione oxalateHCID 198987572-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl bromide2×

Product 1

HCID 19898747
1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]-piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione
Yield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 1.5 ml of N,N-dimethylformamide, there were reacted 0.31 g of the previously obtained 2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl bromide (Compound 9), 0.2 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3) and 0.4 ml of triethylamine at 100° C. for 1 hour. The resultant reaction solution was poured into ice water and then extracted with chloroform. The resultant chloroform layer was then washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Afterward, the resultant residue was recrystallized from ethanol and hexane to obtain 0.30 g (yield 68%) of 1,3-dimethyl-6-(4-[2-(2-phenyl-4-oxo-4H-1-benzopyran-7-yl)oxyethyl]-piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the nonoxalate of Compound 10).

Workup

  1. customThe resultant reaction solution
  2. extractionextracted with chloroform
  3. washThe resultant chloroform layer was then washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAfterward, the resultant residue was recrystallized from ethanol and hexane

Sources & evidence

ORD record
ord-229b00d8eace477e849c1f2f1b21db16
Source dataset
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05114941

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes