Pyridine → 6-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone

HRID 1463

Reaktionsgleichung

Reaktionsgleichung von HRID 1463
[NH2:1][C:2]([CH2:4][C:5]1[C:6](=[O:22])[N:7]([CH2:19][C:20]#[CH:21])[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]=1[CH2:11][CH3:12])=O.N1C=CC=[CH:25][CH:24]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1.CCOCC>[CH2:11]([C:10]1([CH2:24][CH3:25])[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:7]([CH2:19][C:20]#[CH:21])[C:6](=[O:22])[CH:5]1[CH2:4][C:2]#[N:1])[CH3:12]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 196906705-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone2×

Produkt 1

HCID 196906746-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinoneAusbeute 49,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred suspension of 0.25 g (0.85 mmol) of 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 275) in 12 mL of THF was cooled in an icebath and 0.15 mL (1.9 mmol) of pyridine was added followed by 0.13 mL (0.92 mmol) of trifluoroacetic anhydride. The mixture was stirred in the ice bath for 4 h, diluted with 80 mL of ether, washed with 20 mL of saturated aqueous NaHCO3 and dried over MgSO4. Removal of the solvent left 0.24 g of crude product as a yellow solid. Flash chromatography on 30 g of silica gel, eluting sequentially with 50, 75 and 100% ether in hexanes afforded 0.13 g of 6-ethyl-5-cyanomethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 277) as a white solid, m.p. 178°-180° C. 1 H-NMR (CDCl3) 1.3(3H,t), 2.4(1H,t), 2.75(2H,q), 3.75(2H,s), 4.6(2H,d), 7.55(3H,m), 7.7(2H,m).

Aufarbeitung

  1. additionwas added
  2. washwashed with 20 mL of saturated aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft 0.24 g of crude product as a yellow solid
  6. washFlash chromatography on 30 g of silica gel, eluting sequentially with 50, 75 and 100% ether in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b5423c5215ee415abe3ef0b650a1ea4e
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726124

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