Hydrochloric Acid → HCID 19898731, compound

HRID 1196715Notes

Reaction equation

HRID 1196715 reaction equation
CC1C(=O)C2C(OCCCBr)=CC=CC=2OC=1.CN1C(N2CCNCC2)=CC(=O)N(C)C1=O.Cl.Cl.[CH3:36][N:37]1[C:42]([N:43]2[CH2:48][CH2:47][N:46]([CH2:49][CH2:50][CH2:51][O:52][C:53]3[C:58]4[C:59](=[O:64])[C:60]([CH3:63])=[CH:61][O:62][C:57]=4[CH:56]=[CH:55][CH:54]=3)[CH2:45][CH2:44]2)=[CH:41][C:40](=[O:65])[N:39]([CH3:66])[C:38]1=[O:67]>O1CCOCC1.C(N(CC)CC)C>[CH3:36][N:37]1[C:42]([N:43]2[CH2:44][CH2:45][N:46]([CH2:49][CH2:50][CH2:51][O:52][C:53]3[C:58]4[C:59](=[O:64])[C:60]([CH3:63])=[CH:61][O:62][C:57]=4[CH:56]=[CH:55][CH:54]=3)[CH2:47][CH2:48]2)=[CH:41][C:40](=[O:65])[N:39]([CH3:66])[C:38]1=[O:67]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 19898730HCID 19898730, compoundHCID 19898793HCID 19898793, compound2×

Product 1

HCID 19898731HCID 19898731, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

In 50 ml of dioxane, there were heated under reflux 1.78 g of the previously obtained, 3-(3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl bromide (Compound 2), 1.34 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3) and 1.5 ml of triethylamine for 2 hours. After cooling and then filtration, the resultant filtrate was concentrated under reduced pressure, and the resultant residue was then dissolved in chloroform, washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The thus obtained residue was purified through a silica gel column chromatograph (chloroform:methanol=100:2 to 100:10 in volume ratio) and then recrystallized from ethanol and ether in order to obtain 2.40 g (yield 91%) of 1,3-dimethyl-6-(4-[3-(3-methyl-4-oxo-4H-1-benzopyran-5-yl)oxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-hydrochloride of Compound 4).

Workup

  1. temperatureunder reflux 1.78 g of the
  2. custompreviously obtained
  3. temperatureAfter cooling
  4. filtrationfiltration
  5. concentrationthe resultant filtrate was concentrated under reduced pressure
  6. dissolutionthe resultant residue was then dissolved in chloroform
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe thus obtained residue was purified through a silica gel column chromatograph (chloroform:methanol=100:2 to 100:10 in volume ratio)
  11. customrecrystallized from ethanol and ether in order

Sources & evidence

ORD record
ord-f116f5aa7fb94dedb9ebb2de8395b873
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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