Sodium Hydroxide → 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 1463240

Reaktionsgleichung

Reaktionsgleichung von HRID 1463240
C([O:3][C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:9]([CH2:18][C:19]#[CH:20])[C:8](=[O:21])[C:7]=1[CH3:22])=[O:5])C.[OH-].[Na+]>C(O)C.C1COCC1>[C:4]([C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:9]([CH2:18][C:19]#[CH:20])[C:8](=[O:21])[C:7]=1[CH3:22])([OH:5])=[O:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 196907226-ethoxycarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

Produkt 1

HCID 196907156-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinoneAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1.81 g (6.1 mmol) of 6-ethoxycarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 100 mL of ethanol and 50 mL of THF was added 50 mL of 5% aqueous sodium hydroxide. The mixture was stirred at room temperature for 24 h and rotovapped to remove the bulk of the organic solvents. The residue was diluted with 50 mL of 5% aqueous sodium hydroxide and washed with 100 mL of ether. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with two 100 mL portions of ethyl acetate. The combined ethyl acetate extracts were washed with 50 mL of brine, dried over MgSO4 and concentrated to leave 0.87 g (53%) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone as a brown oil.

Aufarbeitung

  1. customto remove the bulk of the organic solvents
  2. additionThe residue was diluted with 50 mL of 5% aqueous sodium hydroxide
  3. washwashed with 100 mL of ether
  4. extractionextracted with two 100 mL portions of ethyl acetate
  5. washThe combined ethyl acetate extracts were washed with 50 mL of brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2eade42f334b4beea015a3c079a00310
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300477

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