Hydrochloric Acid → 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone

HRID 1463248

Reaktionsgleichung

Reaktionsgleichung von HRID 1463248
[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:22][C:23]#[CH:24])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]3OCC[O:18]3)[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].Cl.CCOCC.O>C(OCC)(=O)C.CCCCCC>[CH2:1]([C:3]1[C:4](=[O:25])[N:5]([CH2:22][C:23]#[CH:24])[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=2)=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 218084975,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone

Produkt 1

HCID 196906845,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinoneAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of 2.3 g (6.8 mmol) of 5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone in 1 mL of ethyl acetate was added 50 mL of 6M hydrochloric acid and the mixture was stirred for 4 hours. The reaction was followed by gas chromatography and TLC(20% ethyl acetate in hexane). Upon completion of reaction, 75 mL of ether and 150 mL of water were added to the reaction mixture. The layers were separated and the aqueous layer was extracted twice with 50 mL of ether. The organic layers were combined, dried over MgSO4 and concentrated to yield 1.73 g of 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone (Compound 69) as a yellow oil (86%), which solidified on standing. Mp.=82°-86° C. 1H-NMR (CDCl3) δ1.25(6H,m), 2.4(1H,t), 2.65(4H,q), 4.6(2H,d), 7.7(1H,t), 8.05(2H,m), 8.25(1H,s), 10.15(1H,s).

Aufarbeitung

  1. additionwere added to the reaction mixture
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with 50 mL of ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-05e89660e98c45938ddcf136e316991d
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300477

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