Hydrochloric Acid → HCID 19898767, compound

HRID 1196722Notes

Reaction equation

HRID 1196722 reaction equation
N1C=CC(C2OC3C=CC=C(OCCCOS(C)(=O)=O)C=3C(=O)C=2)=CC=1.CN1C(N2CCNCC2)=CC(=O)N(C)C1=O.Cl.Cl.Cl.[CH3:46][N:47]1[C:52]([N:53]2[CH2:58][CH2:57][N:56]([CH2:59][CH2:60][CH2:61][O:62][C:63]3[C:68]4[C:69](=[O:79])[CH:70]=[C:71]([C:73]5[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=5)[O:72][C:67]=4[CH:66]=[CH:65][CH:64]=3)[CH2:55][CH2:54]2)=[CH:51][C:50](=[O:80])[N:49]([CH3:81])[C:48]1=[O:82]>O1CCOCC1.C(N(CC)CC)C>[CH3:46][N:47]1[C:52]([N:53]2[CH2:54][CH2:55][N:56]([CH2:59][CH2:60][CH2:61][O:62][C:63]3[C:68]4[C:69](=[O:79])[CH:70]=[C:71]([C:73]5[CH:78]=[CH:77][N:76]=[CH:75][CH:74]=5)[O:72][C:67]=4[CH:66]=[CH:65][CH:64]=3)[CH2:57][CH2:58]2)=[CH:51][C:50](=[O:80])[N:49]([CH3:81])[C:48]1=[O:82]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 19898766HCID 19898766, compoundHCID 19898784HCID 19898784, compound2×

Product 1

HCID 19898767HCID 19898767, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

In 50 ml of dioxane, there were heated under reflux for 4 hours 2.12 g of 3-[2-(pyridine-4-yl)-4-oxo-4H-1-benzopyran-5-yl]oxy-1-methanesulfonyloxypropane (Compound 24), 1 ml of triethlamine and 1.95 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3). The resultant reaction solution was then concentrated, and the resultant residue was dissolved in chloroform and then washed with water. Afterward, the water-washed chloroform layer was dried over anhydrous sodium sulfate and then purified through a silica gel column chromatograph (chloroform:methanol=100:1 to 100:15 in volume ratio) and then recrystallized from ethanol, thereby obtaining 2.36 g (yield 83%) of 1,3-dimethyl-6-(4-[3-[2-(pyridine-4-yl)-4-oxo-4H-1-benzopyran-5-yl]oxypropyl]pyperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-hydrochloride of Compound 25).

Workup

  1. customThe resultant reaction solution
  2. concentrationwas then concentrated
  3. dissolutionthe resultant residue was dissolved in chloroform
  4. washwashed with water
  5. washAfterward, the water-washed chloroform layer
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. custompurified through a silica gel column chromatograph (chloroform:methanol=100:1 to 100:15 in volume ratio)
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d1ffb31aa99e4935a7fa32e78658308f
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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