Water → 6-ethyl-5-(2-hydroxyethyl)-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 1460

Reaktionsgleichung

Reaktionsgleichung von HRID 1460
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([CH2:15][C:16]#[CH:17])[C:5](=[O:18])[C:4]=1[CH2:19][C:20](OC)=[O:21])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1.CCOCC>[CH2:1]([C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:6]([CH2:15][C:16]#[CH:17])[C:5](=[O:18])[C:4]=1[CH2:19][CH2:20][OH:21])[CH3:2]

Komponenten

6

Edukt 3

HCID 962WaterHCID 196906976-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone2×HCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 196907176-ethyl-5-(2-hydroxyethyl)-2-phenyl-3-propargyl-4(3H)-pyrimidinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 1.35 g (4.4 mmol) of 6-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 105) in 30 mL of THF was cooled in an ice bath and a slurry of 0.10 g (2.6 mmol) of lithium aluminum hydride in 10 mL of ether was added. The ice bath was allowed to melt and the reaction mixture was stirred at room temperature for 3 h. An additional 0.05 g (1.3 mmol) of lithium aluminum hydride was added. The mixture was stirred for 1 h at room temperature. The mixture was poured into 100 mL of water and 100 mL of ether and allowed to stand for 1 h. The layers were separated and the aqueous layer was extracted with 100 mL of ethyl acetate. the combined organic extracts were washed with 50 mL of 5% aqueous NaOH and dried over MgSO4. Removal of the solvent left 1.36 g of crude product as an amber syrup. Flash chromatography on 30 g of silica gel, eluting sequentially with 20, 40, 60, 80 and 100% ethyl acetate in hexanes afforded 6-ethyl-5-(2-hydroxyethyl)-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 274) as an oil. 1H-NMR (CDCl3) 1.2(3H,t), 2.35(1H,t), 2.65(2H,q), 2.90(2H,t), 3.85(2H,t), 4.55(2H,d), 7.5(3H,m), 7.7(2H,m).

Aufarbeitung

  1. stirringThe mixture was stirred for 1 h at room temperature
  2. waitto stand for 1 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with 100 mL of ethyl acetate
  5. washthe combined organic extracts were washed with 50 mL of 5% aqueous NaOH
  6. dry with materialdried over MgSO4
  7. customRemoval of the solvent
  8. waitleft 1.36 g of crude product as an amber syrup
  9. washFlash chromatography on 30 g of silica gel, eluting sequentially with 20, 40, 60, 80 and 100% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d39e19c8619b4440b84b2d542c14fa6e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726124

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