Pyridine → 6-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 2400105

Reaktionsgleichung

Reaktionsgleichung von HRID 2400105
[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]#[CH:18])[C:6](=[O:19])[C:5]=1[CH3:20])([OH:3])=O.Cl.[CH3:22][NH:23][CH3:24].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH3:22][N:23]([CH3:24])[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]([CH2:16][C:17]#[CH:18])[C:6](=[O:19])[C:5]=1[CH3:20])=[O:3]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10473Dimethylamine, hydrochlorideHCID 10868DicyclohexylcarbodiimideHCID 196907156-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

Produkt 1

HCID 196906856-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinoneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 0.87 g (3.2 mmol) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone, 0.32 g (3.9 mmol) of dimethylamine hydrochloride and 2 mL of pyridine in 10 mL of THF was added 0.74 g (3.6 mmol) of solid N,N'-dicyclohexylcarbodiimide. The mixture was stirred at room temperature for 4 days and filtered to remove insoluble material. The filtrate was diluted with 150 mL of ethyl acetate, washed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous sodium bicarbonate and dried over MgSO4. Removal of the solvent left 0.40 g of crude product which was purified by flash chromatography on a 30 g column of silica gel, eluted with 60, 80 and 100% ethyl acetate in hexanes to furnish 0.30 g (32%) of 6-dimethylaminocarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (compound 19), mp 137°-140 ° C. 1H-NMR (CDCl3)δ2.15(3H,s), 2.40(1H, t), 3.00(3H,s), 3.10(3H,s), 4.65(2H,d), 7.55(3H,m), 7.70 (2H,m).

Aufarbeitung

  1. filtrationfiltered
  2. customto remove insoluble material
  3. additionThe filtrate was diluted with 150 mL of ethyl acetate
  4. washwashed with 50 mL of 5% aqueous HCl and 50 mL of saturated aqueous sodium bicarbonate
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent
  7. waitleft 0.40 g of crude product which
  8. customwas purified by flash chromatography on a 30 g column of silica gel
  9. washeluted with 60, 80 and 100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b90d5da9bb994eaa9e77be86ea5132d6
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05453414

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