Triethylamine → HCID 19898735, compound

HRID 1196721Notes

Reaction equation

HRID 1196721 reaction equation
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[C:10]3[C:14]([O:18][CH2:19][CH2:20][CH2:21]Cl)=[CH:15][CH:16]=[CH:17][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:23][N:24]1[C:29]([N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[CH:28][C:27](=[O:36])[N:26]([CH3:37])[C:25]1=[O:38].C(N(CC)CC)C>CN(C)C=O.[Br-].C([N+](CC)(CC)CC)C>[CH3:23][N:24]1[C:29]([N:30]2[CH2:35][CH2:34][N:33]([CH2:21][CH2:20][CH2:19][O:18][C:14]3[C:10]4[C:11](=[O:13])[CH2:12][CH:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[O:8][C:9]=4[CH:17]=[CH:16][CH:15]=3)[CH2:32][CH2:31]2)=[CH:28][C:27](=[O:36])[N:26]([CH3:37])[C:25]1=[O:38]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×HCID 19898777HCID 19898777, compound2×

Product 1

HCID 19898735HCID 19898735, compound

Reagents, catalysts & solvents 2

HCID 6285Tetraethylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide, reaction was carried out at 100° C. for 8 hours among 2.5 g of the previously obtained 2-phenyl-5-(3-chloropropoxy)-4-oxo-2,3-dihydro-4H-1-benzopyran (Compound 20), 1.2 g of 1,3-dimethyl-6-(piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (Compound 3), 1.0 g of tetraethylammonium bromide and 2.0 ml of triethylamine. The resultant reaction solution was concentrated under reduced pressure, and the residue was then dissolved in chloroform, washed with water, dried over anhydrous sodium sulfate, and then purified through a silica gel column chromatograph (chloroform:methanol=40:1 in volume ratio), thereby obtaining 0.80 g of 1,3-dimethyl-6-(4-[3-(2-phenyl-4-oxo-2,3-dihydro-4H-1-benzopyran-5-yl)oxypropyl]piperazine-1-yl)-2,4(1H,3H)-pyrimidinedione (the non-oxalate of Compound 21).

Workup

  1. customThe resultant reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. dissolutionthe residue was then dissolved in chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. custompurified through a silica gel column chromatograph (chloroform:methanol=40:1 in volume ratio)

Sources & evidence

ORD record
ord-8faeb1e6316a45b09b234ea920ceaa9b
Source dataset
uspto-grants-1992_05
Patent number
US05114941

Reaction notes

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