Oxalate → HCID 19898733, compound

HRID 1196716Notes

Reaction equation

HRID 1196716 reaction equation
CC1OC2C=CC=C(OCCCBr)C=2C(=O)C=1C.CN1C(N2CCNCC2)=CC(=O)N(C)C1=O.C([O-])(=O)C([O-])=O.C(O)(=O)C(O)=O.[CH3:47][N:48]1[C:53]([N:54]2[CH2:59][CH2:58][N:57]([CH2:60][CH2:61][CH2:62][O:63][C:64]3[C:69]4[C:70](=[O:76])[C:71]([CH3:75])=[C:72]([CH3:74])[O:73][C:68]=4[CH:67]=[CH:66][CH:65]=3)[CH2:56][CH2:55]2)=[CH:52][C:51](=[O:77])[N:50]([CH3:78])[C:49]1=[O:79]>C(N(CC)CC)C.CN(C)C=O>[CH3:47][N:48]1[C:53]([N:54]2[CH2:55][CH2:56][N:57]([CH2:60][CH2:61][CH2:62][O:63][C:64]3[C:69]4[C:70](=[O:76])[C:71]([CH3:75])=[C:72]([CH3:74])[O:73][C:68]=4[CH:67]=[CH:66][CH:65]=3)[CH2:58][CH2:59]2)=[CH:52][C:51](=[O:77])[N:50]([CH3:78])[C:49]1=[O:79]

Participants

7

Reactant 4

HCID 71081OxalateHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 19898732HCID 19898732, compoundHCID 19898792HCID 19898792, compound2×

Product 1

HCID 19898733HCID 19898733, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

To 2 ml of N,N-dimethylformamide were added 0.78 g of the previously obtained 3-(2,3-dimethyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl bromide (Compound 6), 0.9 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3) and 3 ml of triethylamine, and the solution was then heated at 100° C. for 3 hours in order to carry out reaction. The resultant reaction solution was treated and then purified in the same manner as in Example 1-(2) to obtain 0.96 g (yield 84%) of 1,3-dimethyl-6-(4-[3-(2,3-dimethyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-oxalate of Compound 7).

Workup

  1. customreaction
  2. customThe resultant reaction solution
  3. additionwas treated

Sources & evidence

ORD record
ord-363f3e01ee04469ea5d77a4113ccf7fd
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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